best cruising sailboat for chesapeake bay

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Cruising Sailboats for the Chesapeake Bay

There’s no better way to experience all the Chesapeake has to offer, cruising in a warm breeze with friends and family aboard the Club’s J/32’s, J/105’s, and Beneteau 33.  Being a member of the Club makes this dream a reality – and for far less money than ownership, charters or renting a sailboat.  Take a mini-vacation or an extended cruise with your family and friends using the Club’s cruising sailboats.  Your boat is ready and waiting for you!

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Best Boat for Cruising Chesapeake Bay: Gear, Maintenance, and Local Insight

Imagine gliding through the calm waters of Chesapeake Bay, the sun warming your skin and a gentle breeze tousling your hair. But wait, you’re missing one crucial element for this idyllic scene – the perfect boat. Finding the best boat for cruising Chesapeake Bay can be a daunting task with so many options available.

Picture this: you’re torn between a sleek sailboat or a sturdy powerboat, unsure which one suits your cruising style best. The right choice can make all the difference in your boating experience, from comfort to efficiency on the water.

Key Takeaways

• Understanding the Chesapeake Bay waters is crucial, with diverse weather patterns and navigational challenges to consider.
• When selecting a boat for cruising the bay, focus on key features like size, stability, shallow draft, maneuverability, and comfort amenities.
• Sailboats are ideal for a serene eco-friendly experience, while powerboats offer speed and convenience.
• Catamarans provide stability and spaciousness, enhancing the cruising experience on Chesapeake Bay.
• Equip your boat with essential gear like navigation tools, safety equipment, anchoring aids, and maintain it regularly for optimal performance.
• Choose marinas wisely, explore prime anchorage spots, follow cruising etiquette, and regulations for a safe and enjoyable experience on the bay.

Understanding the Chesapeake Bay Waters

Geography and weather patterns.

Navigating the Chesapeake Bay requires an understanding of its vast expanse and varied weather patterns. From the Susquehanna River in the north to the Atlantic Ocean in the south, the bay spans over 200 miles and offers diverse sailing conditions. In the summer, you can expect warm temperatures and moderate winds, ideal for leisurely cruising. However, be prepared for sudden thunderstorms, especially in the afternoons. In contrast, the winter can bring cold temperatures and strong northerly winds, making protective harbor choices crucial for safe boating.

Navigational Challenges

When cruising the Chesapeake Bay, you’ll encounter various navigational challenges that demand attention to detail. The bay’s numerous tributaries, shallow waters, and shifting sandbars require a keen understanding of charts, tide tables, and local knowledge. Be aware of the potential for shallow depths in some areas, necessitating a draft-appropriate vessel for navigating safely. Additionally, strong currents, such as those near the Bay Bridge, can affect your boat’s maneuverability, emphasizing the importance of precise navigation and seamanship skills.

Key Features of a Chesapeake Bay Cruiser

When choosing a boat for cruising Chesapeake Bay, there are specific features you should focus on to ensure a smooth and enjoyable journey. Let’s explore the key characteristics that make a boat well-suited for navigating the diverse conditions of Chesapeake Bay.

Size and Stability

For cruising Chesapeake Bay, opt for a boat that strikes a balance between size and stability. A boat that is sufficiently large provides comfort and space for longer trips, accommodating essential amenities without feeling cramped. At the same time, ensure the boat offers stability in various weather conditions prevalent on the bay, such as sudden squalls or choppy waters. A stable boat enhances safety and minimizes motion sickness, ensuring a pleasant cruising experience.

Shallow Draft and Maneuverability

Given the shallow waters and narrow channels of Chesapeake Bay, prioritize a boat with a shallow draft and excellent maneuverability. A boat with a shallow draft can navigate shallow waters without running aground, enabling you to explore secluded coves and tributaries. Additionally, good maneuverability allows you to navigate tight spots, handle strong currents, and dock easily, enhancing your overall boating experience on the bay.

Comfort Amenities and Space

When selecting a boat for cruising Chesapeake Bay, consider the comfort amenities and available space onboard. Look for features that enhance comfort during extended trips, such as cozy sleeping quarters, a functional galley for preparing meals, and a clean restroom facility. Sufficient space to relax and move around comfortably is crucial for enjoying your time on the water. Prioritize boats with well-designed layouts that maximize space and offer convenient amenities to meet your needs while cruising the bay.

By focusing on these key features – size and stability, shallow draft and maneuverability, as well as comfort amenities and space – you can choose a boat that is well-suited for exploring the beauty and challenges of cruising Chesapeake Bay. Prioritize safety, comfort, and functionality when selecting your Chesapeake Bay cruiser to ensure memorable and enjoyable boating experiences on this iconic waterway.

Top Boat Types for Cruising Chesapeake Bay

When considering the best boat types for cruising Chesapeake Bay, it’s essential to match your preferences and requirements with the right vessel. Here are some top boat types to consider for your cruising adventures on the Bay:

Sailboats: For the Sailing Enthusiast

If you enjoy harnessing the power of the wind and the timeless romance of sailing, a sailboat is a fantastic choice for cruising Chesapeake Bay. Sailboats offer a serene and eco-friendly way to navigate the waters while providing a sense of connection with nature. Their quiet operation allows you to enjoy the sounds of the sea and the Bay’s wildlife.

When selecting a sailboat for cruising Chesapeake Bay, consider vessels with moderate to deep drafts that can handle the Bay’s varying depths. Look for sailboats with versatile rigging options to adjust to the Bay’s ever-changing wind conditions. Additionally, prioritize boats with comfortable living quarters for extended stays on the water.

Powerboats: Speed and Convenience

For those seeking speed and convenience in their cruising experience, powerboats are an excellent choice for exploring Chesapeake Bay. Powerboats offer the advantage of faster travel times, allowing you to cover more ground and visit multiple destinations in a shorter period. They are ideal for day trips or weekend getaways on the Bay.

When opting for a powerboat for cruising Chesapeake Bay, look for vessels with efficient engines that provide a good balance of speed and fuel economy. Consider boats with amenities such as cabin space, galley facilities, and comfortable seating areas for a luxurious experience on the water. Prioritize powerboats with shallow drafts for easy maneuvering in the Bay’s shallower areas.

Catamarans: Stability and Space

Catamarans are an excellent choice for cruising Chesapeake Bay, offering unparalleled stability and generous living space for onboard comfort. These twin-hulled vessels provide a smooth and stable ride, making them ideal for those prone to seasickness or looking for a more stable sailing experience. Catamarans offer ample deck space for lounging and entertaining while taking in the Bay’s scenic views.

When choosing a catamaran for cruising Chesapeake Bay, prioritize vessels with shallow drafts to access the Bay’s shallower coves and tributaries. Look for catamarans with spacious cabins, well-equipped galleys, and comfortable amenities for extended cruising trips. Consider catamarans with efficient sail plans for optimizing wind power while sailing on the bay.

By selecting the right boat type that aligns with your preferences and cruising needs, you can enhance your Chesapeake Bay experience and create lasting memories on its beautiful waters.

Reviewing the Best Boats for Cruising Chesapeake Bay

Top sailboat options.

When selecting a sailboat for cruising Chesapeake Bay, you’ll want to consider vessels that offer a balance of performance, comfort, and style. Sailboats are ideal for those who appreciate the tranquility of wind-powered travel and the connection to nature it provides. Here are some top sailboat options that are well-suited for navigating the waters of Chesapeake Bay:

• Island Packet 35 : Known for its sturdy construction and comfortable interior, the Island Packet 35 is a popular choice among sailing enthusiasts. With a spacious cockpit and ample storage, this sailboat offers both performance and livability for extended trips on the bay.
• Catalina 385 : The Catalina 385 combines modern design with excellent sailing capabilities. Featuring a well-appointed interior and a user-friendly layout, this sailboat is perfect for comfortable cruising while enjoying the scenic views of Chesapeake Bay.
• Hanse 418 : If you’re looking for a sleek and stylish sailboat with impressive performance, the Hanse 418 might be the right choice for you. With its innovative design and quality craftsmanship, this vessel provides a thrilling sailing experience while exploring the bay.

Best Powerboats on the Market

For those seeking speed, convenience, and luxury while cruising Chesapeake Bay, powerboats are the way to go. These vessels offer a faster mode of travel, ensuring you can cover more ground and visit various destinations in style. When selecting a powerboat for bay cruising, consider the following top options:

• Boston Whaler 350 Realm : The Boston Whaler 350 Realm is a versatile and reliable powerboat known for its smooth ride and premium amenities. Equipped with cutting-edge technology and comfortable seating, this vessel offers a luxurious experience while exploring the waters of Chesapeake Bay.
• Sea Ray Sundancer 320 : With its elegant design and spacious deck layout, the Sea Ray Sundancer 320 is an excellent choice for those looking for comfort and performance in a powerboat. This vessel provides a peaceful and enjoyable cruising experience, making it a popular option for bay explorations.
• Grady-White Freedom 375 : The Grady-White Freedom 375 combines quality construction with innovative features, making it a top contender for bay cruising. Known for its stability and versatility, this powerboat ensures a safe and enjoyable journey through the picturesque waters of Chesapeake Bay.

Leading Catamarans for Bay Cruising

Catamarans are favored for their stability, spaciousness, and smooth sailing experience, making them an excellent choice for cruising Chesapeake Bay. These vessels offer ample deck space, comfortable accommodations, and impressive performance on the water. When considering catamarans for bay cruising, explore the following leading options:

• Lagoon 450 : The Lagoon 450 is a popular choice among catamaran enthusiasts for its spacious layout and excellent cruising capabilities. With multiple cabins, a large saloon, and a well-equipped galley, this vessel provides a luxurious and comfortable experience while exploring Chesapeake Bay.
• Fountaine Pajot MY 37 : Offering a perfect blend of style and functionality, the Fountaine Pajot MY 37 is a top catamaran for bay cruising. With its modern design, panoramic views, and exceptional stability, this vessel ensures a relaxing and enjoyable journey through the waters of Chesapeake Bay.
• Leopard 50 : The Leopard 50 catamaran stands out for its innovative design, impressive performance, and spacious living areas. Featuring a contemporary interior, expansive deck space, and advanced navigation systems, this vessel delivers a premium cruising experience for exploring the beauty of Chesapeake Bay.

Essential Gear and Accessories for Chesapeake Cruising

Navigation tools and electronics.

When cruising Chesapeake Bay, having the right navigation tools and electronics is crucial. Equip your boat with a GPS system to accurately track your position and plan your routes effectively. A depth finder will help you navigate shallow waters safely, especially in the bay’s varying depths. Consider investing in a VHF marine radio for communication with other vessels and emergency services if needed. Having a reliable compass onboard is also essential for traditional navigation, providing backup in case of electronic failures.

Safety Equipment and First Aid

Prioritize safety while cruising on Chesapeake Bay by ensuring your boat is equipped with essential safety gear. Life jackets for every passenger are a must-have, with additional throwable flotation devices for emergencies. Fire extinguishers should be readily accessible in case of onboard fires. Equip your boat with flares, a signaling mirror, and a whistle for distress signaling. A comprehensive first aid kit is vital for addressing minor injuries or medical emergencies that may occur while at sea. Regularly check and maintain your safety equipment to ensure functionality.

Anchoring and Docking Aids

Efficient anchoring and docking aids can make your cruising experience on Chesapeake Bay smoother and more enjoyable. Have a reliable anchor with the appropriate chain and rope for securely anchoring your boat at various locations in the bay. Consider investing in a windlass to automate the process of raising and lowering the anchor, reducing strain on you and your crew. Fenders and dock lines are essential for safe and secure docking at marinas or anchorages. Have extra lines and fenders on board in case of unexpected docking situations. Familiarize yourself with proper anchoring and docking techniques to handle different conditions effectively.

Equip your boat with these essential gear and accessories to enhance your cruising experience on Chesapeake Bay and ensure safe and enjoyable journeys on the water.

Boat Maintenance and Upkeep in the Bay Environment

Regular cleaning and anti-fouling.

To keep your boat in top shape for cruising Chesapeake Bay, regular cleaning is essential. You should clean the hull, deck, and sails to prevent the buildup of dirt, grime, and salt. Use a gentle boat soap and a soft brush to avoid damaging the surfaces. Additionally, anti-fouling paint can help prevent marine growth on the hull, improving your boat’s performance and fuel efficiency. It’s recommended to apply anti-fouling paint annually or as needed based on usage.

Engine and Sail Care

Maintaining your boat’s engine and sails is crucial for a smooth cruising experience on Chesapeake Bay. Regularly check the engine for oil levels, coolant, and belt tension. Change the engine oil and filters as per the manufacturer’s recommendations. Ensure the sail’s integrity by inspecting for wear and tear, especially at the seams and corners. Lubricate the sail tracks and furling systems to prevent rust and ensure smooth operation. Proper care of your engine and sails will extend their lifespan and improve overall performance while out on the water.

Local Knowledge: Marinas, Anchorages, and Cruising Tips

Choosing the right marina.

When it comes to selecting a marina for your cruising adventure on the Chesapeake Bay, consider factors like location, amenities, and services offered. Opt for a marina that is conveniently located near key attractions or your preferred cruising routes. Look for marinas that provide facilities such as fuel docks, pump-out stations, showers, and laundry services to ensure a comfortable and convenient stay.

Ensure the marina has proper security measures in place to protect your vessel while you’re out exploring the bay. Additionally, inquire about the availability of transient slips if you’re planning a shorter visit or require flexibility in your docking arrangements. By choosing the right marina, you can enhance your overall cruising experience on the Chesapeake Bay.

Prime Anchorage Spots

Exploring the Chesapeake Bay offers a plethora of picturesque anchorage spots where you can relax and take in the beauty of the surroundings. Popular anchorages like Annapolis, St. Michaels, and Oxford provide stunning waterfront views and easy access to charming towns with local shops and restaurants.

Consider anchorages that offer protection from prevailing winds and sea conditions to ensure a tranquil night’s rest aboard your boat. Plan your itinerary to include a mix of secluded anchorages for quiet nights under the stars and bustling harbors for a taste of local culture and cuisine. Remember to check for any anchoring restrictions or guidelines in certain areas to ensure you’re anchoring responsibly and respecting the marine environment.

Cruising Etiquette and Regulations

Before embarking on your cruising journey along the Chesapeake Bay, familiarize yourself with common cruising etiquette and regulations to ensure a safe and harmonious experience for yourself and other boaters. Maintain a safe distance from other vessels, especially in crowded areas, and yield the right of way as needed to prevent accidents and navigate smoothly.

Observe speed limits in designated areas and be mindful of no-wake zones to minimize your impact on the environment and respect local regulations. Proper waste disposal is crucial to safeguarding the bay’s ecosystem, so be sure to follow guidelines for trash disposal and holding tank management. By practicing good cruising etiquette and adhering to regulations, you can contribute to preserving the natural beauty of the Chesapeake Bay for future generations to enjoy.

You’ve learned about the key aspects of choosing the best boat for cruising Chesapeake Bay. From essential gear and maintenance tips to the significance of local knowledge and prime anchorage spots, you’re now well-equipped for a memorable boating experience on the bay. Remember to prioritize regular cleaning, engine care, and respecting cruising etiquette to ensure a safe and enjoyable journey while preserving the bay’s ecosystem. Happy cruising!

Frequently Asked Questions

What factors should i consider when selecting a boat for cruising chesapeake bay.

Consider the boat’s size, draft, and hull design for navigating shallow waters, as well as sufficient storage for gear and provisions.

Why is regular cleaning important for a boat cruising in Chesapeake Bay?

Regular cleaning prevents the build-up of salt and grime that can corrode or damage your boat’s surfaces and equipment.

What is anti-fouling, and why is it necessary in Chesapeake Bay?

Anti-fouling is a protective coating applied to the boat’s hull to prevent marine growth, such as barnacles, which can slow down the boat and increase fuel consumption.

How should I maintain the engine of my boat in the bay environment?

Regularly service the engine, check oil levels, inspect for leaks, and ensure proper ventilation to prevent overheating.

Why is sail maintenance crucial for cruising Chesapeake Bay?

Proper sail maintenance ensures optimal performance and longevity, reducing the risk of unexpected issues while sailing in varying wind conditions.

What local knowledge is essential when choosing a marina in Chesapeake Bay?

Consider the marina’s location, facilities, services, and reputation, as well as its proximity to prime cruising destinations and protection from rough weather.

What are some prime anchorage spots in Chesapeake Bay?

Annapolis and St. Michaels are popular anchorage spots known for their picturesque settings, historical charm, and sheltered waters.

Why is it important to practice cruising etiquette and regulations in Chesapeake Bay?

Adhering to cruising etiquette and regulations ensures a safe and enjoyable experience for all boaters and helps protect the bay’s ecosystem from potential harm.

Hi, I'm Richard, a passionate traveler and cruise enthusiast. With over a decade of experience exploring the world's oceans, I've developed a deep love for all things related to cruising. Whether it's luxury liners or intimate river cruises, I enjoy sharing my insights and tips to help others plan their perfect getaway. When I'm not sailing the seas, you can find me writing about my adventures or planning my next voyage

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Top 13 Chesapeake Bay Cruising Destinations

Aug 26, 2020

One of the big advantages of owning an inflatable boat is the ability to travel where you want, whenever you want, to enjoy a day of sailing. If you're a Maryland, Virginia, or D.C. resident, you have access to one the world's best cruising destinations, the Chesapeake Bay.

From fishing and national parks to delicious food like crabs and oysters, the Chesapeake Bay has a lot to offer. Covering over 4,000 square miles, there is plenty to explore. Below you'll find the top 13 Chesapeake Bay cruising destinations.

1. St. Michaels

Located on Maryland's Eastern Shore, St. Michael's, Maryland has plenty to offer despite being home to a little over 1,000 people. Home to the Chesapeake Bay Maritime Museum , several art galleries, restaurants, and other historic landmarks, St. Michaels is also a prime cruising destination. Located on the water, St. Michael's is a perfect place to access the Chesapeake and it offers up some wonderful views.

2. Galesville

Located on the western shore of the bay, Galesville is a small town that sits along the West River. A steamship line in Galesville used to connect Annapolis and Baltimore, and the town was once home to many Chesapeake Bay Watermen. It is now a hot spot for pleasure boating and home of the West River Sailing Club and Hartge Yacht Harbor

Located along the Tred Avon and Choptank Rivers, Oxford, Maryland is home to the Oxford-Bellevue Ferry, the Tred Avon Yacht Club, and the Oxford Museum . The ferry is believed to be the oldest privately owned ferry, with service dating back to 1836. In addition to its local attractions, Oxford access to the Tred Avon and Choptank makes it a great cruising destination for sailors and boaters alike.

Located 40 minutes south of Annapolis, Deale, MD provides many scenic views of the Chesapeake, making it a popular destination with boaters. Home to waterfront bars and open-air crab houses, Deale is perfect for anyone looking to hit the open water for the day and then enjoy a good meal afterwards.

5. Solomons Island

Located at the mouth of the Patuxent River, Solomons Island was the home of many 19th century shipyards that supported the local fishing economy. Today, Solomons Island is home to many marinas, seafood restaurants, the Calvert Marine Museum , and the Annmarie Sculpture Garden & Arts Center . Its position along the waterfront make it a prime destination for cruising.

6. Rock Hall 

The jewel of the Upper Eastern Shore, Rock Hall, MD is a picturesque cruising destination. Serving as the hub for Kent County's maritime industry, Rock Hall is home to the Rock Hall Yacht Club, over a dozen marinas, various charters, boat rentals, and more! A day of cruising in Rock Hall will give you access to beautiful scenery and plenty of open water to explore.

7. Chestertown

Located along the Chester River, Chestertown was once one of the six Royal Ports of Entry and considered Maryland's second leading port. Today, Chestertown is home to Washington College, a number or restaurants and historic attractions. Offering a wide range of scenic and historic sailing views, Chestertown is a perfect location for day cruising.

8. Kent Island

The largest island in the Chesapeake, Kent Island, is nestled between Annapolis and the Eastern Shore of Maryland. The Cross Island and South Island trails provide plenty of outdoor activities across the island. For those looking to cruise the open waters, Kent Island offers unique access to the Eastern Bay, Chester River, and the heart of the Chesapeake Bay itself.

9. The Wye River

With easy access to fishing and crabbing destinations, the Wye River is a favorite cruising destination for many. Add in the Wye Island Natural Resource Management Area, and you have a perfect destination for cruising and exploring the outdoors.

10. Baltimore

Baltimore's Historic Inner Harbor is the mouth of the Patapsco River. With access to a number of marinas, the Inner Harbor is a great launch point for day cruising. Enjoy views of historic Federal Hill and Fort McHenry in the Harbor, and as the Patapsco opens up into the bay, you'll find additional outdoor destinations such as North Point State Park and Fort Smallwood Park.

11. Annapolis

Sometimes referred to as the Sailing Capital of the U.S., Annapolis is home to various boat shows, the Naval Academy, and the National Sailing Hall of Fame. Its position along the South River, Severn River, and the Chesapeake Bay make it a great launch point for cruising.

12. Washington DC

The beautiful Potomac River runs directly through the Nation's Capital, making Washington, D.C. a prime destination for sailors. With access to historic views in the heart of D.C. to a variety of parks and outdoor destinations, D.C. is a great place to spend a day out on the water.

13. Havre de Grace

Sitting at the mouth of the Susquehanna River and the head of the Chesapeake, Havre de Grace is uniquely positioned to several state parks and scenic views including Elk Neck State Park and Susquehanna State Park. With easy access to the water and the outdoors, Havre de Grace is a worthwhile destination for anyone looking to explore the bay.

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Looking for a Chesapeake Bay Boat

• Thread starter DanFleig
• Start date Aug 16, 2016
• Forums for All Owners
• Ask All Sailors

Sailboat Owners, What boats would you recommend for a family brand new to cruising in the Chesapeake Bay? We’re an Active Duty Military family, with a budget limited to $60K or less. For Family (Crew), I only plan on having myself, my wife Ali, and 3 year old Heidi on board, which means it’ll be important that I can single hand the boat 95% of the time. I only have limited sailing experience. I grew up sailing with my dad in FL and have sailed a 1985 Hunter 23 on the Bay for the last 2 years (and learned a LOT of hard lessons). I’ve been looking at Tartan 37’s because of their seaworthy reputation, and enough room for my wife and I to expand our family. We’d like to use the aft double berth as a “Baby Room” (when necessary, hopefully next year) when sailing. I’ve also looked at some Beneteau 321’s because they’re affordable, and comfortable looking for short trips. I do worry about them not having enough storage areas though…. What would you all recommend? We have a house on the South River, and will not be living on the boat full time, but plan on taking 1-2 trips max. When I retire in 6 years, we’d like the option to either cruise the Caribbean or cross the pond to the Mediterranean, but we don’t necessarily need to own a boat now that can do that (unless the price is right). What sort of minimum equipment should we be looking at, I think the longest trip I’d dare to take right now is from the South River to Virgina Beach and back…. Though I want to use the boat I purchase to practice for longer (and offshore) trips. I appreciate your feedback! Dan  

Dan; You are shopping in the biggest boat market in the Mid Atlantic - lots of boats out there. While I doubt you will be able to find a seaworthy Tartan 37 I understand why you would like one, they are great cruisers! My suggestion would be to retain a trustworthy and experienced buyers broker. If you PM me I will give you the name of a great independent local broker that you can speak to. Good luck and welcome to Annapolis  

One thing you'll want to consider is the draft of the boat. While I don't know the Chesapeake I am aware that there is some thin water there. If you buy a boat with too much draft you'll either miss some great cruising or be constantly afraid of running aground. That's certainly true around here. 5' draft is about the maximum. Unfortunately, most modern cruisers in the 30+ length draw around that or more - especially if they have any performance in their pedigree. Also, look for a fractional rig for shorthanded handling. They typically have a small headsail that can easily tacked which is really important in your situation. The main sail is easily adjusted with the backstay for power so you'll have a lot of control right there at the helm. There is no way you are going to want to haul in a big jib every time you want to change direction. This is a BIG item that isn't often discussed. After my wife had Chemo-therapy and radiation therapy there was no way she could do it. That made me crew and her the helm. That's fine but when the wind piped up she would get scared. We sold that boat for that reason. Don't ignore the cat boats. For example the Non Such line or the traditional Cat boats such as Marshall. They typically have enormous room below and just the one sail to handle. On the Non Such the unstayed fiberglass mast bends off in higher wind, effectively depowering the rig. The Cat boats have very good stability because of their width and they don't draw a lot of water - most are centerboarders. I hope I given you some food for thought. You are sure to hear from others with their ideas. BTW I like the Tartan 37 (The old centerboard one).  

Dan a Tartan 37 or other similar cruisers are not the kind of boat that you would take out for a couple of hours pleasure ride. These are boats designed for the open seas and are just not responsive enough to make them enjoyable in protected waters. It would be like driving a bus to go to the mall. I think that what you may need for the next 5 years is a boat in the 30' to 32' range that can be easy to single hand and inviting to take out at a moments notice for an evening sail. It would provide adequate room and stability for short trips and would be much less expensive to operate . I do understand that in the Bay there are military marinas that offer real affordable rates but even when visiting other towns you will not pay as much for a transient slip. Consider insurance costs and maintenance expense and the savings over 5 years will be a good chunk of money. You should be able to find a production boat in good condition for less than 50% of your budgeted amount. A shallow draft boat will expand your destination options. Purchase well, take good care of it and in 5 years you could probably sell it for what you paid for it and then go seek your heavy cruiser.  

look at the reviews in Good Old Boat and on the Boat US website: With your budget you could afford a well maintained 28-36' Pearson, Seafarer, Cape Dory, Ericsson, or S 2. I would not put a wife and 3 year old on a Marshall cat : wind comes up, you've forgotten to reef, and your family will be terrified.  

I agree with the 5 foot draft limit. Since you looked at a B321, maybe look at a B323, my model. The wife will love "the bathroom, not a head" as people say. 4'9", elect fridge, standup room in the VEE. I can g9ve you oodles of DIY to add storage. I think a couple are still in the owner's mods.  

Bad Obsession

Hrm....There are tons of good answers here. You really have to consider how you plan to use the boat and what section of the Bay you will be on. There is a bit of a difference between the Northern Bay, the Middle Bay, and the Southern Bay. How long do you plan on being out at a time? How serious is your family about cruising with you? Do you plan to anchor or go into a slip? What features do you have to have? What features would be nice to have? What features can you live without? Answer those questions before boat shopping. You also want to find a boat with a good diesel that is in good shape. Check out the sails while you are on here because that could be a refit item that runs a bit in cost. Here is something to consider. You say your budget is about $60K. That means that you need to keep your boat purchase closer to $50K because you will need left over money to refit the boat. When you are seriously looking at boats consider what money you will need for the refit. Another thing to consider is your yearly budget. The longer the boat, the fatter the budget needs to be. If the boat needs a lot of work then that could dip into your budget. Find a marina that you want to keep your boat and find out the prices, the depth of the slips, the property tax for the area you will be living in, and all of the hidden costs. Can you find a DYI marina or do you have to pay the marina to do a bottom job for you? The bay has a lot of shallow water, as others have said. Keep your draft less than 5 feet. I have spend most of my life on the Chesapeake Bay and I have even worked on the water when I was a kid. I know most of the Bay pretty well but my knowledge is a fleeting second compared to others around here. That being said, there are TONS of places to go, things to see, and things to do. There are great special event. Also, Tangier Island and Smith Island are a must see. The summers can be brutal!! You want to have a bimini and probably a dodger. If you single hand a good autopilot is a must! Someone has mentioned a Pearson. These are good boats but know what you are getting into before you get it. Get a good survey because, while they were well made, they haven't been made in some time. This is true for most boats that you are looking at. You mentioned a Tartan 37. They too are good boats but I would really get it inspected well. If it is a centerboard then really have that checked. Personally the centerboard would make me a bit nervous. One other thing to know is that, while it is a nice boat and sails well along with a good reputation, the cabin may not be as big as other 37 foot boats. Another boat to look at is a Catalina 34. They are good sailing boats, have a really good cabin layout, and perform well. My Uncle has been sailing an MK I Catalina 34 around for the last 10 years or so. You may be able to find an MKii Catalina 34 in your budget. Actually, don't concentrate on the make/model of the boat right now. Figure out what you want and need and then find something to match that as close as possible. All boats are compromises.  

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Chesapeake Bay Boating Guide: Cruising America’s Largest Estuary

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Last Updated on November 29, 2023 by Boatsetter Team

Cruising the Chesapeake Bay by boat can be a lifetime endeavor since there is so much to see and do in America’s largest estuary. The bay is nearly 200 miles long and anywhere from 3 to 30 miles wide. Its shoreline is over 11,000 miles, and about half of the bay’s 8,100 square miles of watery surface is in Maryland and half in Virginia. 

The Bay spills from the Susquehanna River source in the north down to the Atlantic near Norfolk, Virginia leaving thousands of anchorages and 150 rivers to explore! In our Chesapeake Bay Boating Guide , we’ll explore:

• Things to do  
• Best time of year to boat on Chesapeake Bay  
• What to look out for 

Explore boats & on-water experiences in Chesapeake, VA

Things to do at Chesapeake Bay

Perhaps the best-known town on the Bay is Annapolis with its renowned sailboat show , the prestigious Naval Academy, countless museums, and dozens of quaint eateries. It makes a great place from which to launch an exploration. 

Approximately 25 miles southeast of Annapolis lies St. Michaels, a seaside resort on Maryland’s eastern shore. St. Michaels is a must-see for history buffs, crab lovers, and amateur photographers looking for inspiration because this place never takes a bad picture. 

In the summer, the population of St. Michaels swells beyond its 1,500 permanent residents, and getting a guest dock is like winning the lottery so you won’t be alone anchoring out on the Miles River in 15-30 feet of water. Visit the outstanding Chesapeake Bay Maritime Museum with its 18 acres of exhibits and restored boats on display.  

Farther south around Tilghman Island and up the Tred Avon River is Oxford, one of Maryland’s oldest towns. There are lots of wonderful bistros and restaurants like Schooners and The Masthead but save room for dessert because if you leave Oxford without stopping at Scottish Highland Creamery, you’d have missed possibly the entire reason to be here. This ice cream shop is hardly more than a window front but serves homemade frozen treats to die fo r.

Cross the bay and head down to Solomons Island, another former boatbuilding and seafood packing town that today is a tourist magnet. Jutting out between Back Creek and the Patuxent River, Solomons is connected to the mainland by a long causeway. 

Less than 1 ½ miles long and in parts just the width of a two-lane road, the island has a long wooden boardwalk that takes you up to the Calvert Marine Museum with its Drum Point screwpile lighthouse and narrated tours on an 1899 bugeye boat. In the 1880s, more than 500 locally built boats made up the Solomons fishing fleet and by the 1930s, the town specialized in building wooden pleasure yachts.   

At the bottom of the Bay, you’ll find Norfolk, which is part of the largest shipping port on the East Coast. Naval vessels, commercial ships, and recreational boats all share the same waters, and Mile Marker Zero, the official beginning of the Intercoastal Waterway (ICW), marks the beginning of the 1,200-mile journey to Florida and beyond. 

For more than two centuries, Norfolk has been a Navy town, and today, you can still tour the naval base. A must-visit is the Nauticus, a multi-level maritime museum designed to educate as well as entertain. The USS Wisconsin is berthed next door and dwarfs the surrounding buildings. It was a veteran of three wars and the last battleship built for the U.S. Navy. 

Best time of year to boat on Chesapeake Bay

Summers can be sweltering and winters freezing but the shoulder seasons of spring and fall are phenomenal. In April to May and September to October, the crowds are small, and the weather is usually perfect for boating. 

What to look out for

The Chesapeake is a fairly protected body of water, but it can get boisterous. Northerly winter storms kick up large square waves that build the entire length of the shallow Bay and become quite serious in the southern parts. Also, it’s very easy to wrap a prop on one of the ubiquitous crab pots or ground in the shallows. Keep a good lookout and rest easy knowing that the Bay is nearly all soft mud which shouldn’t cause too much damage to your keel . Pro tip: If this is your first time on a boat or have little experience, we strongly recommend booking a boat with a USCG-certified captain . 

Pro tip: Rent a boat for your Chesapeake Bay boat trip!

The Chesapeake Bay is a unique place begging to be explored by boat. It’s also great for a corporate event, a birthday party, a sailing regatta or a romantic sunset outing. Book a boat with a USCG-certified captain for a local guide, or take the helm on a bareboat—Find all options on the peer-to-peer (P2P) boat rental marketplace.  

There are dozens of boat rentals in the Boatsetter fleet with locations from Baltimore, to Annapolis and Deltaville to Norfolk. And if you’re in town for the boat show, staying on a boat will save you a bundle due to skyrocketing hotel prices.

You’ll be back

The vast Chesapeake Bay can’t be seen in a day, a week, or even a month. You’ll want to come back again and again to stay in the towns, fish the rich waters , and watch sunsets from secluded anchorages. Once is definitely not enough. 

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Zuzana Prochazka is an award-winning freelance journalist and photographer with regular contributions to more than a dozen sailing and powerboating magazines and online publications including Southern Boating, SEA, Latitudes & Attitudes and SAIL. She is SAIL magazines Charter Editor and the Executive Director of Boating Writers International. Zuzana serves as judge for SAIL’s Best Boats awards and for Europe’s Best of Boats in Berlin. 

A USCG 100 Ton Master, Zuzana founded and manages a flotilla charter organization called Zescapes that takes guests adventure sailing at destinations worldwide. 

Zuzana has lived in Europe, Africa and the United States and has traveled extensively in South America, the islands of the South Pacific and Mexico. 

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Best Boat for the Chesapeake Bay?

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Maybe an impossible question to answer, but just for fun...what boat/boats would you select for sailing the Chesapeake (only the bay) and why? (cost not matter)  

A boat no greater than 32ft that draws no more than 5ft. Why?? Because that's all one needs to day sail, cruise or occasionally circumnavigate Delmarva.  

As I see it, the three characteristics of the Chesapeake are light winds, shoals, and chop. Bad: heavy, deep draft, long overhangs Good: High SA/disp, moderate draft, short overhangs, reliable engine.  

Well reasoned analysis.  

If boat would only be used on the Chessie for weekend and up to weeklong Cruises, I would go for a light air performer. Maybe a J-boat or: Sunfast 3200 2009 Jeanneau 3200 Sun Fast Sail Boat For Sale - www.yachtworld.com  

Keels on the Bay Even though our fin keel limits where we can sail on the Bay and rules out some marinas, we wouldn't change it. I'd rather be able to plow through most spots where we touch than dig in with a wing keel and be stuck there until whenever.  

I like the idea of a keel boat having a center board as well. That would include my little Tartan 27', the Tartan 34 and some 37's as well. The center board acts as a kind of depth alarm which is easily raised. The pervasive feature of the Chessy is skinny water so it's best to have a good way of dealing with that.  

CalebD said: I like the idea of a keel boat having a center board as well. Click to expand...

A Gemini. Of course.  

Gunboat 66!  

I've had the romantic idea to restore and convert a Skipjack to a comfortable family cruiser. If I had the $$ it would be an interesting project. I have seen one, I think it was on the Sassafras? I find our current boat is pretty ideal with a 4'2" draft with c/b and respectable light wind performance, but lacks some things I would like such as a swim platform, island berth, larger cockpit...  

Why don't you see more multi's one the bay? Cost? Seems there are not many marinas capable of handling a wide multi as well, the only one I know around me is Pleasure Cove Marina & Club. Edit: in regards to haulout.  

T37Chef said: Why don't you see more multi's one the bay? Cost? Seems there are not many marinas capable of handling a wide multi as well, the only one I know around me is Pleasure Cove Marina & Club. Click to expand...

There are quite a few Cats around the Chessy if you look for them but I think cost and difficulty finding slips probably does temper their appeal a good bit.. The relatively narrow beam and modest purchase cost (for a cat anyway) of the Gemini probably goes a long way explain why they're pretty popular on the Bay. A Gemini will fit any slip that would take the larger monohulls. Big cats are pricy even in relation to the big monohulls you see more and more on the Chessey, but you have to figure a 45' cat probably has the space of a 80' monohull. Cats are attractive to me for the room and comfort, shallow draft and speed on certain points of sail. That said, I've yet to see a cat that my eye really loved like it does certain monohulls.  

midlifesailor said: That said, I've yet to see a cat that my eye really loved like it does certain monohulls. Click to expand...

Horn Harbor Marina, way down on the outside of Virginia's Middle Peninsula, markets itself specifically as catering to large cats. Last I was down there, though, it was for sale and the business seemed to be suffering. A shame, actually, because it's actually a pretty nice facility in a very nice location.  

Answer: the one you sail. Get off the dock! *grin* Starting from scratch I'd want something with a high L/B for good speed, lots of sail area, and a lifting keel (not a centerboard). Definitely head at the base of the companionway and a good sized wet locker. Big sail locker in the foredeck to launch a chute for light air. Hard dodger with opening windows. Screens on everything. In the meantime I'll keep sailing the bottom off Auspicious, gunkholing by braille, and enjoying myself.  

Hylas 56....ok.wake up I kinda like our C&C 35 for the bay. Easy to handle for a couple, and fun to take trips in ( We take her to new England every year). Quicker than many similar sized and even larger boats and very well balanced ( You sailed her Shaun)....very good to windward....4'6 the 7'6 with the CB down so you can go in shallows or go for stability to windward when the wind blows hard. Safe when heeled with handholds and bracing points ( dont like huge sprawling cockpits or salons with no handholds). Masthead rig so you can downwind sail without worrying about ripping the main up. Good sail area.. I love to play on the cats...like the entertainment of the salon...but the sleeping areas dont have enough ventalation for me unless you get to giant size.. Dave  

chef2sail said: Hylas 56....ok.wake up I kinda like our C&C 35 for the bay. Easy to handle for a couple, and fun to take trips in ( We take her to new England every year). Quicker than many similar sized and even larger boats and very well balanced ( You sailed her Shaun)....very good to windward....4'6 the 7'6 with the CB down so you can go in shallows or go for stability to windward when the wind blows hard. Safe when heeled with handholds and bracing points ( dont like huge sprawling cockpits or salons with no handholds). Masthead rig so you can downwind sail without worrying about ripping the main up. Good sail area.. I love to play on the cats...like the entertainment of the salon...but the sleeping areas dont have enough ventalation for me unless you get to giant size.. Dave Click to expand...

Catalina 22 Capri-good for single handing? Wondering if I could get some thoughts on this: I'm thinking of buying a new or late-model Catalina Capri 22, but was wondering how easy they are to single hand. Main concern: raising and lowering mainsail in windy conditions. I used to own an S2 22' and sold it for lots of reasons, but partially because it was frustrating to tie off the tiller, go forward to undo halliard and on that boat you had to really tug a lot to get the sail all the way down. Often in heavier winds, this took so long that the wind would push the boat around, and I'd have to run back and point her back into the wind, before scampering up to the mast again to try to finish the job. A similar problem was encountered while raising the sail. Well, that was my first boat, and I've only sailed larger boats with roller-furling mains and autopilots since. I'm getting a little nostalgic for the nice simple kinda sailing again though, and the Capri seems to be a nice economical idea. Also, I'm interested in any general feedback present or former owners of this model may have. Thanks.  

You're gonna laugh, but... Fales Navigator.  

A Catamaran of any size. Marc  

A monohull with a swing keel like my Clearwater 35 allows you to get yourself out of a grounding and gunkhole where similar sloops simply can't go.  

Probably slice them like butter... ... but the post-flood floating trees and dock parts would be touble.  

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The largest and at most famous estuary in the United States, Chesapeake Bay (or “the Chesapeake”) is truly an extraordinary place. Stretching across six states and the District of Columbia, the Bay watershed never ceases to amaze with its rich history, vital economic importance, and astounding beauty. And the wonders of sailing the Chesapeake Bay could fill a lifetime.

The history, natural beauty and wonderful ecosystem combine to present visitors with endless possibilities, and there’s a new adventure around every corner. However if you only have a limited amount of time to explore, it’s best to get an understanding of what there is on offer before your trip.

The following are a couple of tips for planning your sailing adventure on the bay.

How to Stay (Find Airbnbs & Hotels)

Here is an interactive map of hotels and airbnbs you can book in the Chesapeake area.

Be Realistic

If you try to see everything, it’s likely that you’ll miss a lot. Considering the scale of Chesapeake Bay , you will have to be realistic. It is not somewhere to speed around trying to encompass it all in one visit.

Do it right, and you will enjoy the experience so much more and thereafter, who knows, you may return to continue the adventure.

Remember the Definition of Cruising

To sail about for pleasure in an unhurried or unconcerned fashion, to move leisurely about an area. Let the Bay dictate your pace, stimulate your interest, suggest stops and places to see.

Be flexible in your approach, do plan, but don’t think that the plans cannot be altered once you arrive.

Summers are hot and humid, whereas Spring and Autumn are long, and much more comfortable. Even being on the Bay cannot always provide sufficient respite from the still humidity of the summer months, so be warned.

How to Travel

Cruising can take two forms. You can charter a vessel either bareboat or crewed .

Bareboat – You take charge of the boat yourself and provide the crew, and if you are a competent sailor, then this may heighten the excitement, but it is also less of a vacation and more of an adventure. Don’t forget also the issue of stopovers, are you mooring, docking, or anchoring the boat!

Crewed – the cruiser is manned with a captain and crew, and you can sit back and enjoy the trip and all the sights without having to worry about any of the mundane logistics and duties.

Itinerary Suggestions

There is simply so much, in a sense too much, to see, so it may be a good starting point to pick a more defined area of the Bay and concentrate on that.

Though you’re looking for variety then sailing the Chesapeake area is a natural cruising route for discovery, made for simply hopscotching from one shore to the next, with things to see, visit, experience, taste and indulge all of your senses at once.

Commonly visited areas include Havre de Grace via the Chesapeake & Delaware Canal built in 1829. Many people choose to visit the inner harbour of Baltimore travelling along the Sassafras River with its steep banks and from there to Rock Hall, a sailors town famed for its seafood; travel from St Michaels to Annapolis, known as the sailing capital of the World ; onward to Oxford on the Trent Avon, a sleepy, quaint and picturesque town, or finally on to Washington DC should the mood take you.

You will find yourself with so many options and avenues of adventure, so many that a sense of spontaneity should be a prerequisite. Whilst you slowly absorb the sights, sounds and scenery as you are cruising, you can smile to yourself and be proud that you chose to sail the Chesapeake Bay.

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20 Comments

Great post, loved the pics! I’ll definitely try to go to Chesapeake!, I’m the kind of person who don’t want to miss anything but I’ll follow your advice “If you try to see everything, it’s likely that you’ll miss a lot.” and as you said, maybe I could return a second time and try to see everything. Thanks for the info! Pilar http://www.thelifestylehunter.com

Thanks Pilar! So glad you enjoyed the post :) Yes, definitely recommend to pick a more defined area of the Bay and concentrate on that if it’s your first time visiting – there really is just so much to see and do that it’s better to do a little and enjoy it fully than try to slam out a lot and enjoy it half as much.

Hope you have an amazing time!

At university I had a friend who was always talking about the wonders of Chesapeake Bay and she made it sound like something I really should do. Many years later, I still haven’t, but your post has reminded me how wonderful it sounded.

So glad we could remind you Sarah! Yes, highly recommend a trip – it’s a beautiful bay with so much to see and do :)

Great tips! You’re so right about the weather. I live in DC and the summers are unbearable. Sailing in the fall is the best time. Annapolis is my favorite place on the bay.

Thanks Jessica :) Awesome to hear you’re already familiar with sailing on the Bay :)

I will go for the bareboat one where you have total control. Loved the suggestions and nice pics.

Awesome Gokul! Glad to hear we’ve inspired you to take a trip :) Let us know how you enjoy the Chesapeake

Really good tips. Would love to do this. I would love to lay out and let someone man the boat.

Thanks Holly – yes, jumping on a crewed boat is great if you’re looking to enjoy the trip and all the sights without having to worry about any of the mundane logistics and duties :)

Happy travels!

This is my home! I was so excited to see my beautiful corner of the world featured!

What an incredible place to grow up! Not bad having Chesapeake Bay as your backyard :) Awesome!

Hey Megan, I once got invited on a boat but the trip never ended up going through as the boat needed tons of work and couldn’t get out of the port. This sounds amazing. I’d prefer warm waters in the Caribbean but I imagine seeing this side of the US would be gorgeous as well. Thanks for the post. Cheers, Jack

Hi Jack, thanks for your comment :) Sorry to hear your boat didn’t end up going out on Chesapeake – totally agree that the Caribbean is an incredible spot for sailing too. Very different experience to the Bay but they both make for great sailing :)

Dear Sir, May 22nd, 2018 I have a 27 ft Bayliner sailboat and I would like to sail from Norfolk to Annapolis and back. I have never done this before but it is something that I really want to try. My daughter lives near Annapolis and is close to the water (West River). I feel that I need some bay sailing but I do know how to sail on lakes (Smith Mountain Lake in VA). I am retired and am a good swimmer. I have no idea as to where one would stop for the night and how long it would take and how safe it is to do this. These are my questions and I would like to talk to your group about lessons and feasibility.

Thanks in advance for your time.

Tim Kute 336-413-6126 [email protected]

Hi Tim, thanks for reaching out. We’re a couple who run a personal blog with tips from our adventures, so unfortunately can’t advise you on things like organizing lessons or your level of experience. I would pose your questions to the team at Annapolis Bay Charters who may be able to offer you more insight. Hope they can help :)

http://www.annapolisbaycharters.net

Hi, Sailing is a life fun for those who live for sail like me.I really like the Sailing tips you share with those who live for sail. its help the new sailors in sailing and boost the moral of the experienced sailors. i appreciate your efforts. One thing i like to add is that don’t forget to protect your hands during sailing with premium quality sailing Gloves.

Glad to hear from a fellow sailor! Great tip on remembering to include gloves in your kit :)

Thanks for this. We are thinking of sailing down from Boston to Chesapeake via canal. We have 6-week sabbatical so plenty of time. We would like to avoid the worst of the summer heat/humidity, what would be best time to go in your opinion?

Also, I’ve heard that there are a lot of shallow spots in the bay, we draw 6′, any specific areas to avoid?

Thanks, Sea Fever

Hi David :)

Re best time to head out, I would say anytime from April until June, after that and once it hits July it gets really humid so I would avoid at all costs.

For good anchorage spots and plannig out your trip, check out the Gunkholers guide to the Chesapeake, it’s a cruise planner with suggested itineraries but also has charts and waypoints for anchorages and key locations. It’s always very up to date too :)

Have an amazing trip!

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Help choosing a boat for Chesapeake Bay!

• Thread starter beauski83
• Start date Apr 20, 2009
• Apr 20, 2009

Hi Everyone, 1st post. There seem to be a lot of knowledgable boaters on this site. I'm very optomistic! I just moved to Annapolis from Meriden, CT. In CT, my dad and I had a 2002 Four Winns 200 Horizon on the CT river. I am looking at purchasing my own boat now that I am down here, but it seems like a 20' boat may be a little "iffy" for the bay. I'm looking to keep the purchase under 20K. Right now I am looking at 2 vastly different boats. 2001 Wellcraft Excalibur 23 and a 2002 Chaparral 216 SSi. I guess my question would be, how big of a boat is "big enough" to handle normal conditions on the bay. I'm just looking for something to cruise around on and explore the area, but at the same time, I don't want to spend most of my day getting tossed around. Any advice would be appreciated...especially by those who are familiar with the bay/south river area. Thanks, Adam  

Lieutenant Commander

Re: Help choosing a boat for Chesapeake Bay! Welcome to iboats, Adam! If you intend to go out only on good days, either boat would work. The question really becomes "How comfortable do I want to be?" A couple additional feet in length makes a big difference. You also need to consider the hull shape. A deeper V will ride softer than a shallow V in rough water. As I'm sure you know, on any given day they'll be many other boats out there, each generating a wake. In addition, the Bay can be VERY unforgiving when the wind and tide are opposing. Just because it's warm and the sun is shining doesn't automatically mean it's a "good" boating day on the Chesapeake. Good luck with your decision.  

Re: Help choosing a boat for Chesapeake Bay! Thanks Arks. I appreciate it. I'm very used to driving a regular bowrider and think I would feel right at home w/ the Chaparral 216 SSi. However, I think, for a few bucks more, the benefits of having the Wellcraft Excalibur may out weigh my lack of familiarity with the style of boat. From what I've read on this site and others is that it handles chop very well. The marina in VA is asking 19,995 for the 2001 Wellcraft Excalibur. It has 296 hours, 7.4 MPI Merc w/ 310 hp. Boat was sold from the same marina in 01, has been kept in the boatel there, and has had all its service done there. Price does not include a trailer. I think if I can get the price down a little bit, I'll be able to pull the trigger. Any advice on where to get a decent trailer? I wont be trailering the boat for very long distances. My neighborhood has a ramp less than a mile from my house. Thanks!  

Lieutenant Junior Grade

• Apr 21, 2009

Re: Help choosing a boat for Chesapeake Bay! Is the Wellcraft a cuddy? Wasn't the excaliber offered in both cuddy and open bow? Anyhow, from your discussion, i guess it's likely a cuddy. For cruising around, some hanging out, etc. the somewhat larger, cuddy would be my choice on that bay. Kids love the ride in the open bow, but if for you, buddies, your dad or whatever, the open bow is more a convenience for docking, etc. Many boat buyers underestimate how much effect rough water can have on their experience. It starts off as an uncomfortable feeling out there sometimes, and winds up being a boat you don't use much! WTrying to go boating based on "is it going to be a nice enough day and low boat traffic" means not boating much! 23', heavy deep v, bigger water boat is my vote. Price? hmmm.... trailer is a good negotiating item. The marina can get one easily, so work on that. Also, salt water, 8 year old boat, raw water cooled?  

Re: Help choosing a boat for Chesapeake Bay! Hi TMH. Thanks for the input. You are correct. The Excalibur is available in a bow rider as well. The BR is considered the "sport" model. The one I am looking at is has the closed cabin. I'd prefer the bow rider, but that raises the price and availability. The boat was kept on the northern Potomac river, which I'm pretty sure is fresh water. It also was kept in a boatel, so it's very clean.  

Frank Acampora

Supreme mariner.

Re: Help choosing a boat for Chesapeake Bay! Well, I cruised down the uppr bay from Conowingo Dam to Annapolis in a 15 foot closed bow. It is do-able BUT: My son was driving and he only knows one speed. When I got home, my butt was actually bruised from bouncing in the seat. 20 feet will do it, there are a lot of them out there and I use a 21 foot cuddy BUT: There is a LOT of traffic on the bay and many times it looks like diamond plate with 2 foot diamonds. Not comfortable even in a 20 footer. Wait until your first experience in "Ego Alley" Annapolis.  

Re: Help choosing a boat for Chesapeake Bay! Thanks, Frank. I'm not sure where "Ego Alley" is, but I've got a pretty good idea of what it must be like. I moved down here without knowing a thing about the area, except that Annapolis remided me of Portsmouth, NH where I lived after college. Beautiful area and for the most part, the people are great. But there are a few I wouldn't mind nudging off the bay bridge! Typically, the boat will get the most use Friday-Sunday. It's crazy how difficult it is to pull the trigger and actually buy a boat! I just want to have a boat that runs well and, on most days, keeps my passenger's and my *** relatively bruise free!  

mickjetblue

Chief petty officer.

• Apr 24, 2009

Re: Help choosing a boat for Chesapeake Bay! makes sense!  

Petty Officer 1st Class

Chesapeake Bay Cruising At Its Best

Spring has finally arrived in the Northeast after a long, cold winter. A light breeze gently sways the few sailboats in the harbor back and forth on their anchors, inviting yet another sailing season in on the Chesapeake Bay.

The local sailors are restless, busily de-winterizing and preparing their craft to get out on the bay at the first opportunity. This scene conjures up memories of the incredible summer we spent cruising on the Chesapeake Bay last year.

Team Zuri Discovers the Chesapeake Bay

The Chesapeake Bay is the largest estuary with the most coastline of any other bay and in fact, its 11,600 miles of shoreline is longer than the entire coastline of the US. With more than 150 rivers feeding the estuary, the shoreline offers a varied landscape from the urbanized cities of Baltimore and Washington DC to the quaint colonial coastal towns of St Michael’s and Cambridge. Its farming and fishing communities on the historic Eastern Shore are tranquil and seem rather untouched by time. There’s an element of timelessness here. These areas are quaint and a little insular, however these people know how to enjoy the watermen’s way of life, including sailing, crabbing or just chillin’ in a boat with a cooler stocked with worms and beer.

Raft-Ups: Bay Cruising at its Best

Our “raft-up” get-togethers started in early May in Spa Creek, Annapolis. With the regal Naval Academy as the backdrop, the beloved “Blue Angels” wowed the crowds with a spectacular air show, officially marking the opening of the summer season on the Bay. The entire harbor was filled to capacity with anything that floats, from homemade rafts to mega yachts. Estimates are anything from 500 to 1000 vessels, further cementing Annapolis’ reputation as the sailing capital of the US. Next up was our 4th of July fireworks raft-up and it was as spectacular and the crowd was as dense. These Marylanders know how to celebrate! Annapolis is infamously known as a “drinking town with a sailing problem” and as Dick Franyo of the Boatyard Bar and Grill in Eastport says, “We know how to throw a party!”

Our local “ringleader” and raft-up organizer was Chris on his Rambunctious , a Post 38 Sportfish. Chris is a local boy who grew up on the bay and he knows every crevice and nook in the bay. He led the way to St. Michaels for another round of 4th fireworks the next day where several of our boat owners and Dream Yacht charter guests joined us. Pretty soon we had a raft of about 10 to 12 boats of different sizes, shapes, and propulsion, with Zuri, our Prout 45 catamaran, acting as the anchor boat. More fireworks followed that night, lighting up the sky amid very excited ooh’s and aah’s from the packed anchorage. The daytime heat forced us into the lukewarm water, drifting leisurely around on floats, cocktails in hand, only coming out for some mega indulgences on local fare. Briny oysters on the half shell, rockfish, spicy Maryland blue crab dip and some juicy steaks to top it off. Yes, we enjoyed every juicy, fresh, and succulent bit of seafood straight from the bay.

The raft-up commune

Sunsets and Pickin’ Crabs

Sun-soaked weekends were the norm throughout the summer. Each weekend was as colorful and interesting as the sunsets on the bay and the lighthouses that dot the Chesapeake. New friends and raft-up buddies joined us at Gibson Island, Dobbins Island, West River, St. Helena Island, South River, Herrington Harbor, and eventually, Rock Hall for the annual “Pirates and Wenches” Party, an epic event! Rum tastings, local seafood, pirate boats and outfits were the order of the day in Rock Hall during the weekend. Known as the “Pearl of the Chesapeake”, Rock Hall is a picturesque fishing town with a rich history dated as far back as 1707.

The lighthouses of the Chesapeake

The fish is served fresh off the decks of the local fisherman and, here outsiders are called “chicken-neckers” but more precisely, it refers to people from the western shore. Their comical attempts at catching crabs with a chicken neck tied to a long piece of string, is looked upon by the locals with amused disdain but to be sure, it provided hours of entertainment for the kids on our raft-ups!

Zuri and sister ship Persistence in Annapolis Harbor

During the summer, we indulged several times in one of the most famous “events” in the Chesapeake: “Pickin'” crabs. Blue crabs are as synonymous with Maryland as lobster is to Maine and serving a crab feast is a matter of local pride in the Chesapeake region. But make no mistake, “pickin’ crabs” is not a meal, it’s a social event. It’s a messy, loud affair and a proper feast takes several hours when done properly. Nowhere is the crab experience more completely local than it is at an old school crab house like “Cantler’s” in Whitehall Bay. This was where we anchored on one of the raft-up weekends and one sultry evening 15 of us dinghied into Cantler’s, excited to attack this local delicacy. We were promptly put on a waiting list. Apparently, this, too, is part of the experience. These crab houses are always chock full and no amount of complaining will speed things up. Like I said, this is an event and people take their time pickin’ these crabs.

We were finally seated, at least an hour or more later at long picnic-style tables and benches. Sitting elbow to elbow with strangers and friends alike, waitresses rushed along, covering the tables with brown butcher paper, placing pitchers of water, rolls of paper rowels, lemon wedges, wooden mallets and small forks around the table, while quickly taking orders for dozens of crabs and beer, and that’s it. The steamed blue crabs, now reddish in color, are unceremoniously dumped on your table, covered in the very spicy, zesty local Baltimorean seasoning called Old Bay. The crabs come by the dozen, and these male-only crabs are steamed, never boiled, in sizes medium, large, jumbo or colossal. Little bowls of vinegar and melted butter for dipping rounds off the meal. We opted for large but by the end of the evening, I wished that we had gone with colossal size, no matter the price. It seemed like a lot of work for very little food even on the large crabs!

Crab pickin’: It starts out fairly civilized but ends up in a heap of messy crab carcasses 

There’s a special learning curve in finding that sweet tender meat and the locals are quick to teach the rookies. It takes a loooong time to learn how to dissect the crab just right to get but one mouthful of crab meat and I realized that I probably should have had an appetizer before the “meal”. This affair gets very messy and noisy as the hammers crack away, the shells and crab juice fly and everyone’s fingers get covered in the very hot red seasoning. Pitchers of Budweiser or Yeungling are served with the crabs, not wine as is usual with seafood, but trust me, you need the beer to put out the flames of the Old Bay seasoning. The menu usually is extensive, but few locals ever eat anything but steamed crabs, corn on the cob and sweet fluffy cornbread or hush puppies. It is an event to behold! Check out this great article: 10 Photos Show Maryland’s Blue Crab Industry Like You’ve Never Seen It Before .

Crab boats in Tangier Island

Remote Chesapeake Bay Cruising Destinations

Tangier Island

Tangier Island is a delightfully unique little community which is slowly disappearing due to erosion and along with it, the Elizabethan English speaking locals. But for right now, it’s one of the friendliest places on earth. The island, with a population of about 700 consisting mainly of the Crockett family or their descendants, is a step back in time. It’s rich in history, blessed with abundant oyster and crab and known as the soft-shell crab capital of the nation. The island can only be reached by boat or plane, which helped preserve this piece of living history. Read more about this unique Island>>

Summers End, But Annapolis Sailing Cruises On

We declare without a doubt, this body of water one of our favorite cruising grounds in the world. Captain John Smith once said of the Chesapeake Bay, that “Heaven and Earth never agreed to frame a better place for man’s habitation.”

Helpful Resources

• Baydreaming Chesapeake Bay Cruising Guide
• waterwayguide.com
• Annapolis Tourist Information
• Chesapeake Bay Magazine
• Port Annapolis Marina
• St Michael’s
• Solomons island
• Tangier Island AND this article from Cruising World Magazine about discovering Tangier Island

Favorite Restauarants

There are so many good and fun restaurants in downtown Annapolis. Be sure to check out several bars and restaurants while you are in town.

• Pusser’s Landing for the “painkillers”
• Dock Street Bar & Grill for the best crab cakes
• Mc Garvey’s Saloon & Raw Bar to meet local sailors
• Middleton’s Tavern & Raw Bar is a great late night piano bar
• Chick & Ruth’s Delli for some patriotism and a fun dining experience

Charter in the chesapeake

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Sail Chesapeake Bay

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Explore the USA's Largest Estuary and Discover America

Living in North America and looking for a bareboat charter destination close to home? Seeking to experience the natural beauty and the modern lifestyle of the USA? Wanting to vacation under sail but not bothered about snorkeling in clear blue tropical waters? Then take a look at Chesapeake Bay as a destination. 

So convenient for the locals and a fascinating place to visit from all over the world, Chesapeake Bay offers lovely summertime conditions for keen sailors and vacationing families. And all around this extensive sunken river valley are exciting places to explore, from secluded bays to modern cities with just about everything this part of USA has to offer.

It All Starts in Annapolis, America's Sailing Capital

Chesapeake Bay is a vast waterway, 200 miles long draining  64,000 square miles in six states via the more than 150 rivers that feed it. In the upper section of Chesapeake Bay you are in Maryland. The state's big city is Baltimore, while the capital is historic Annapolis, your likely starting point on a Chesapeake Bay sailing vacation. Annapolis is a lovely city that lies at the heart of the region's, some would say the nation's, sailing culture. It is also home of the National Sailing Hall of Fame and US Naval Academy - try to spare the time for a tour.

The Chesapeake's Upper Bay

Sailing out of Annapolis, turn the corner and you are immediately far from the bustle of the city. It doesn't take long to get a sense of the geography here – inlet after countless inlet formed as the sea level rose after the last ice age, beyond which wooded lowlands share the landscape with cultivated farm properties and a generous sprinkling of picturesque settlements.

Head south and a huge expanse of tidewater opens up. Bear northeast and sail under the monstrous dual-span Chesapeake Bay Bridge towards Baltimore, or on the eastern shore Rock Hall and the Chester River.

Rock Hall is a pleasant fishing village that offers an overnighting choice on a marina or at anchor in nearby Swan Creek. Just 15 nautical miles from base, getting to Rock Hall is an easy first day's sail. It's also a convenience stepping-off point for an upriver journey in either direction - to Baltimore's Inner Harbor or Chestertown, both with appeal in their own different ways. If you want to spend longer in the Bay's upper reaches, sail up to the Sassafras River and you can easily fill a week-long itinerary without going south of Annapolis. 

But to see more of this huge Bay with its 11,600 miles of shoreline, you need to head back under the big bridge. Immediately south of  Kent Island is Eastern Bay that brings you into the Wye River area. Here St Michaels is a popular stopover, a waterfront village with excellent marina facilities, shops and restaurants catering for the nautical crowd. St Michaels is also home to the Chesapeake Bay Maritime Museum. A short sail further south are Tilghman Island and Oxford, at the mouth of the Choptank River, setting for James A. Michener's great novel Chesapeake. 

This may well be all you have time to see on your Chesapeake Bay sailing vacation. However if you have longer, continue on south, exploring the eastern shore around Crisfield or crossing to Solomons Island if needing supplies or a marina berth.

The Middle Bay and South

Sail by the mouth of the Potomac River and across the state line into Virginia. Call at Smith or Tangier Island for an appreciation of the Chesapeake way of life and the wonderful natural environment in these parts. Most of the residents of Tangier Island make their living from crabbing, one of the Bay's big industries.

As you proceed south, you may wish to stop over at Deltaville for a berth and supplies, before heading across to the up-market coastal resort are of Cape Charles, with all its amenities for young and old. If time is still on your side, you can go as far as Portsmouth, rent a marina and take off by car to explore the area of Newport News, Norfolk and Virginia Beach.

As you sail back to Annapolis, there are numerous top spots you missed on your way out – Onancock,St Leonard's Creek on the Patuxent, and all those other inviting bays and rivers you observed on the way south. So leave plenty of time to stopover and make your return a leisurely sail.

Around these parts there is many a yachtsperson who will talk about sailing on the Chesapeake. How they've been doing it all their lives and still not been into half the bays and rivers. Head out and find your own special place, perhaps it'll be one that even the locals haven't  come across yet.

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Sail Selina II

Relaxing chesapeake bay sailing tours, sailboat rides & sightseeing boat trips in st. michaels, md, we sail april 19,2024 to nov 3, 2024, clean & safe, thank you for supporting small business, our popular st michaels maryland sailing charters and relaxing chesapeake sailboat cruises.

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2 Hour Relaxing Chesapeake Day Sail

Want to relax? Join our friendly crew and learn about St. Michaels while cruising in a comfortable well-maintained historic sailboat on the Chesapeake Bay. Enjoy the sun on your face and the wind in your hair as you sit back, relax, and enjoy outdoor scenery on your personalized sailing boat tour!

Chesapeake Bay Champagne Sunset Sail

Experience a breathtaking Chesapeake Bay sunset while savoring a glass of Champagne or handcrafted beer or wine on this romantic St. Michaels, MD sunset cruise. Book now to embark on an unforgettable journey that’s perfect for couples looking for a unique and romantic date night activity.

Moonlight Cruise

Enjoy free Champagne while taking in the breathtaking beauty of a sunset or the rising of the moon on Chesapeake BY aboard this romantic Moonlight Cruise!

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St. Michaels Wine Tasting Cruise

Come aboard Sail Selina II in St Michaels MD and learn the basics of wine tasting and sample great vintages with Capt. Iris and her crew during this 2hr outdoor excursion.  Our wine cruise is just an hour from Annapolis, making it the perfect day trip.

Beer Tasting Cruises

Looking for a fun and refreshing way to quench your thirst with a cold beer while exploring the St Michaels area? Sit back and enjoy some great Maryland Craft breweries aboard the Selina II!

Private Sailing Lessons

Embark on an unforgettable sailing adventure with our seasoned team aboard the historic yacht Sail Selina II. Experience the freedom and exhilaration of sailing while learning new skills and building confidence on the water. This introduction to the basics that will transform the way you connect with mother nature.

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Marriage Proposal Engagement Cruise

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Nautical Wedding Package

Looking at weddings on a boat? Get married in St Michaels MD on a sail boat and have an unforgettable nautical elopement or sailboat wedding ceremony aboard Sail Selina’s yacht! You have two wedding packages to choose from:  boat weddings are either a Ceremony Under Sail, or a Wharf-Side Wedding.

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Sail Selina has perfected the art of sailing, and now we’re proud to introduce our collectable high-quality logo apparel that will have you looking as good as you feel on the water.

Best Relaxing Luxury Sail Boat Tours on Chesapeake Bay

Looking for a relaxing Saint Michaels, Chesapeake Bay boat tour? Want to get out on the water, unwind and spend some time in nature? If you’re wondering about things to do in St. Michaels MD or seeking top attractions in St. Michaels Maryland, look no further than the luxury sailing yacht Selina II. Unique, upscale, and exclusive, she limits her passengers to just 6 guests for an intimate taste of the history of sailing.

With freshly varnished mahogany, brightly polished brass, and comfortable seating, let Sail Selina II, the premier sailboat in St Michaels, MD, be your sightseeing charter boat. Hop aboard and experience another time and place.

Come join us outdoors on the water for a relaxing 2-hour sailing trip on this nostalgic river boat cruise. Your St Michaels, Maryland sailboat ride includes a personalized informative tour with our knowledgeable 1st-class captains and friendly crew. We know you’ll love all the boating trips aboard our meticulously-restored historic 1926 sailboat Selina II, including romantic sunset cruises, our super popular day sails, and our specialty outings like sailing lessons, wine tasting tours in St. Michaels MD, beer tasting cruises, moonlight sails and more.

For private sailing tours, the Sail Selina II is docked at the Harbour Inn & Marina in the heart of St Michaels, MD, a charming eastern shore town known for its wonderful seafood restaurants and quaint small-town feel.

If you are looking for day trips to St. Michaels Maryland or if you want a sailing charter on the Eastern Shore of the Chesapeake Bay, Sail Selina II’s relaxing sailboat trips are just 90 minutes from Philadelphia, Baltimore and Washington D.C. and just 60 minutes from Annapolis.

Outdoors in nature, our sailing boat offers your choice of a public or a private boat ride in one of the best places to sail. Chesapeake sailing is known for its beauty and gorgeous sunsets. Your sailboat charter includes a boat sail through the harbor and then out into the Miles River for spectacular views and sometimes even wildlife viewing like Osprey & Bald Eagles. This year there have even been porpoise sightings.

Looking to relax? We are the St Michaels MD harbor cruises to choose!

Learn more about the history of our sailboat and all the fun outdoor activities in St. Michaels, MD here:

The #1 Boat Tour in St. Michaels on TripAdvisor!

A friend was visiting from Baltimore and we went sailing last night for the sunset cruise. It was amazing, the sailboat was gorgeous, the Captain and her first mate were exceptional, and the beauty of the river was breath taking. I am so glad I discovered Sail Selina II, I will be taking many friends and family members on this beautiful adventure when they come to visit me in Easton. Thank you for a remarkable memory and such a beautiful experience.

A golden opportunity to sail on a captain owned historic wood yacht! It was a dog day of August with precious little wind, yet we enjoyed every minute of our trip. Captain Iris was a gracious host, passionate generational owner, not only captain but articulate professor of both sailing and ship building. We highly recommend sailing aboard the Selina ll. The crew is fabulous as well.

Hubby and I spent a sunset afternoon on Selina 2 with Captain Iris and first mate Jesus. We had a lovely cruise drinking champagne and listening to Captain Iris talk about St Michael and the history of her family sail boat. What I loved was she was mentoring a future captain in the making - a twelve year old from the area who wanted to learn more about sailing. This is so worth it and I very much encourage you to go!

My wife and I had a great time on this vintage sail boat. The Captain and First Mate were great hosts teaching us a lot about sailing and the history of the bay at the same time. Loved that the boat holds only six guests at a time, only four aboard for our trip, making it a very intimate experience!

The two hour cruise In the company of Captain Iris, Crewman Chris, and four other guests provided the best evening of our August vacation. The generous hospitality (nice selection of wine and beer if champagne was not your preference) was supplemented by the unexpected and pleasant opportunity to observe several races and Captain Iris was generous with her knowledge of sailing the Tred Avon areas of the Chesapeake. The Salina II will see us again when we return.

Took a moonlight cruise on the Sail Selena II. Had a lovely evening star gazing, sipping wine, chatting with the other couple aboard. Cap’t Iris and her ever so sweet (and personable) first mate were both kind and knowledgeable. We enjoyed the evening immensely. We would recommend this outing without hesitation. Such a great experience!

Being a motor-head all of my life never really let me get the deep appreciation of the sea as I experienced when I sailed on the Selina II. To cruise along with nothing but the sound of the waves, wind and seagulls was a truly eye opening experience for me. Captain Iris was absolutely enchanting with the stories of Saint Michaels and her beloved Selina II. The cruise was intimate with only 2 other couples and was an experience I will long remember.

Captain Iris runs a fabulous operation out of St. Michaels. This was our first time visiting the town and this was such a great way to experience St. Michaels and the Chesapeake. The Sunset Champagne cruise was fun and intimate as only 6 people maximum. The two other couples we met were so sweet. Sail Selina II is a must do in St. Michaels!

Why Sail Selina II?

Rated #1 on tripadvisor.

When looking for things to do in St Michaels MD, o ur reviews tell the story! Limited to just six guests, Sail Selina II is ranked the #1 Maryland sail boat tour in St. Michaels and has been for 18 years running.

Everything Is Included

Sit back and relax. Want a drink? We’ve got it! Cold beer, red & white wines, Champagne, and soda are available for sale on all our Maryland sailboat rides and are included on our evening charters.

Over 96 Years of Experience

Sail Selina’s top-notch skippers have a combined sailing history of 90+ years, and her friendly crew has a combined sailing history of 30+ years. We all love to sail and we love taking people for sailboat rides!

Spacious & Beautiful Boat

All our relaxing sailing boat charters are in a gorgeous setting. Sail Selina II was built as a gentleman’s yacht in the Gatsby era and is finished in freshly varnished mahogany and brightly polished bronze. Her spacious cockpit is the perfect setting for a Maryland sail on the ultimate charter boat in St Michaels, MD. Join us for a sailing charter boat tour and unwind with an authentic taste of the history of sail.

The Best Captains

Our St Michels boat tour captains are known for their storytelling skills and offer a boat trip balanced with some touring, some sailing, and some time to simply relax, unwind and kick back. When sailing on the Chesapeake in St Michaels, choose from a basic sailboat ride, or opt for a specialty outing like a local craft brew beer tasting cruise or a sunset champagne charter.

Best Sailing Destinations Chesapeake Bay

Last Updated by

Daniel Wade

May 9, 2023

‍ Key Takeaways

• The best sailing destinations in the Bay will vary based on your desired water activity
• A sailing trip in the Bay offers scenic views with great food and rich maritime culture
• Annapolis is the sailing capital of the world and gives Florida a run for its money
• Choosing the right boat is key to ensuring a safe travel and comfortable experience
• Summer months might be crowded so be sure to research the best opportunity for you

‍ Arguably one of the best sailing destinations, Chesapeake Bay, boasts beautiful scenery. But what are some of the best Chesapeake Bay sailing destinations?

The best sailing destinations in Chesapeake Bay are Annapolis and St. Michaels along with Norfolk. Other locations worth checking out are Solomons Island and Rock Hall as well as Smith Island. Keep in mind you need to travel the eastern shore of Maryland and Virginia to see all of these locations.

In my experience there is not much that compares to sailing in Chesapeake Bay. Annapolis is America’s sailing capital of the world for a good reason and is a great place to start.

Table of contents

‍ The Top 15 Best Sailing Destinations in Chesapeake Bay

Chesapeake Bay is quite popular for showcasing the natural beauty and a rich marine history. It has turned into a global sailing destination that offers plenty of exciting experiences for sailors of all kinds.

You can explore many top locations for a sailing adventure but it is recommended to start around Annapolis in Maryland since it is dubbed the sailing capital. Annapolis in general features picturesque villages and plenty of water locations to explore. Keep in mind that weather and navigational conditions vary across the bay.

Annapolis in Maryland is the renowned sailing capital for a good reason. It enchants sailors with the United States Naval Academy and has a rich marine history that features the famous Annapolis Boat Show.

Annapolis offers a lot of opportunities for sailors to dock and explore. This Chesapeake Bay harbor town allures with its scenic beauty. Below you can see other key attractions to this area.

• Abundant amenities to meet your needs
• Bustling harbor filled with marinas and boatyards
• Tons of restaurant possibilities

St. Michaels

St. Michaels has turned into a charming location due to its history and abundant sailing community. Be sure to bring a camera along this eastern shore town that showcases a beautiful harbor and Victorian homes. The town also is home to the Chesapeake Bay Maritime Museum where you can dedicate you time to check out the rich history and vibrant culture of the bay and its waterways.

Norfolk is a bustling harbor city on the Chesapeake Bay's southern coast that boasts a rich naval history as the site of the world's largest naval base. Sailors flock to this cultural hub that is renowned for various options below.

• Museums with rich history
• World-class restaurants

Numerous marinas throughout these cruising destinations grant convenient access to sheltered waters. This creates an opportunity for exciting city explorations.

Solomons Island

Solomons Island is another charming and historic town in southern Maryland that sits on the Patuxent River near the Chesapeake Bay. Its protected harbor attracts many sailors and its waterfront park and lighthouse offer scenic beauty.

There are an array of restaurants and shops to check out while staying at one of many marinas. Solomons Island proudly welcomes visitors to explore and unwind.

Rock Hall can be found on Chesapeake Bay's eastern shore where you will likely see an entire village of people fishing. It is loved by many for its natural elegance and wonderful waters.

Sailors that are drawn to crabbing or fishing experiences will want to stop here. The Chesapeake Bay Environmental Center is another additional location to check out since it offers educational programs to enlighten those about its history.

Deltaville offers fully equipped marinas and comprehensive maritime services that are complemented by a charming center for delightful strolls. Solomons' southbound boats often cross the Potomac River while navigating Virginia's Northern Neck rivers and creeks to reach Reedville or Deltaville in Virginia. Explore the vast waters of Great Wicomico or seek shelter in the protected haven of Mill Creek and capture the essence of the Southern Chesapeake.

Smith Island

Smith Island is a perfect sailing location. Those that are wanting to visit this Chesapeake Bay island must visit by boat since it is the only habitable island in Maryland.

There are three different villages in this location but they each offer clear waters and a calm sailing experience. This island is also famous for its Smith Island Cake.

Wye River has a combination of urban and marine areas that allow you to find peaceful surroundings. Wye Island and its 2,800-acre nature preserve are remarkable features that you cannot find anywhere else.

Tuckahoe State Park is one of these beautiful locations that you can check out after sailing. You also have a good chance to see amazing creatures in their natural habitats such as a bald eagle or blue heron. If you have a small enough boat you can explore more areas that are not accessible with larger sailboats.

Tangier Island

Tangier Island is in the Chesapeake Bay's south and is home to serious fishing opportunities. It is also home to the Tangier History Museum that will allow you to check out the island's culture.

There are plenty of boat tours that you could take to experience crabbing or fishing trips if you do not want to on your own boat. The area has secluded waters that make a great escape from reality.

Onancock is another Chesapeake Bay town considered a gem on the Virginia eastern shore. They too have a historic allure and that is coveted by a scenic harbor with a vibrant cultural heritage.

If you are wanting to experience a feeling like home then Onancock is a great opportunity. They have a tight knit community that engages in a lot of fishing and sailing. You can also see a beautiful sunset from many of the docks of your choosing.

Delaware Bay

Delaware City is located at the northern tip of Delaware Bay . This small community can be reached on foot from Delaware City Marina. This used to be a shallow salt marsh but the river becomes more wooded as you go upstream and offers a secure anchoring location with sufficient water depth and swinging space.

The western end of Cape May Canal marks the start of the harbor approach from Delaware Bay.

This expansive and exposed body of water stretches in a Southeast to Northwest direction. Before crossing Delaware Bay it is crucial to carefully check the weather forecast and can be an exhilarating journey under favorable conditions but caution is necessary in this particular area.

Kent Island

Kent Island is located in the heart of the Bay and shows off tons of rich marine history. It is surrounded by sheltered waters and it draws in sailors from all over the world.

You can find the Chesapeake Bay Bridge on this island which is a remarkable feat of architecture that connects the Bay's eastern and western shores. The harbor is a great place to hang out and to enjoy some of the best views for a perfect sunset.

Galesville is a delightful bay town on the west bank that once served as a steamship line hub connecting Annapolis and Baltimore. It was also home to numerous Chesapeake Bay watermen.

You will now see that the area is a sought-after destination for leisure boating with the West River Sailing Club and Hartge Yacht Harbor. This small peninsula offers a charming community park that features a 14-mile boardwalk along Riverside Drive and shows off scenic views of the West River.

Reedville is a charming fishing village at Chesapeake Bay's northern tip. It has a rich maritime history and thriving fishing industry to compliment the serene haven which lures sailing enthusiasts to its pristine waters.

When you explore the scenic harbor you can also check out these options below.

• Local boutiques
• Famous eateries
• Captivating heritage of the Chesapeake Bay's fishing traditions

The Patapsco River flows into Baltimore's Historic Inner Harbor and is an ideal starting point for sailing with numerous marinas. Explore the Harbor to admire landmarks like Federal Hill and Fort McHenry.

As the Patapsco opens up into the bay you can discover outdoor attractions such as North Point State Park and Fort Smallwood Park. Baltimore is a must-visit city for sailors that offers Henderson's Wharf Marina in Fells Point for a convenient anchorage near top pubs or taverns and music venues. There are abundant sailing and racing activities along with other limitless opportunities that might leave you feeling that you have only scratched the surface.

Key Benefits and Drawbacks of Sailing in Chesapeake Bay

Sailing in the Chesapeake Bay’s beautiful waters is a sight you have to see. The experience is definitely worth the trouble but some sailors could argue there are some drawbacks. Below are some of the common pros and cons to consider before sailing in the Bay.

• There are plenty of sailing locations to help you find a perfect experience. Each spot has its own appeal catered to sailing, fishing, or food.
• The Bay is famously known for its cuisine. You cannot miss out on the crab cakes and oysters but there are other options too if you do not like fresh seafood.
• There are plenty of secluded waters to explore. This offers sailors the perfect sailing environment no matter where they plan to go.
• You will find many marine historic sites and landmarks. This is a perfect opportunity for history buffs to brush up.
• You will be able to see various forms of wildlife like dolphins and bald eagles.
• There are a handful of expensive overnight dockage fees at certain Bay marinas that increase the cost of sailing in the area compared to other destinations.
• The Bay's sailing experience is impacted by environmental challenges like pollution and overfishing. This raises concerns about its quality but actions are being taken to currently help clean up the environment.
• Navigating certain areas of the Bay can be challenging. The summer typically has an increase of recreational boats and often creates crowded waters.
• The Bay endures demanding weather with strong winds and rough waters at certain times of the year. This is especially difficult in the winter months.
• Certain sailing spots within the Bay may offer limited access to essential amenities like grocery stores or repair facilities. You should also check in advance to be close to medical services in the event of any issues.

Ideal Boat Types to Sail in the Chesapeake Bay

Choosing the right boat is important for a safe and enjoyable sailing experience in Chesapeake Bay. Your ideal boat type will correlate on your needs and desires as well as the sailing conditions.

It is best if you conduct proper research based on your needs and the boat type you may already have. If you happen to be in the area you could also chat with local sailors to get their opinion.

Chesapeake Bay typically has these popular boat types:

• Daysailers are a perfect boating option designed for casual sailing. Those that are new to sailing generally gravitate to this boat type.
• Cruisers are an appealing sailboat type that offers a comfortable ride and speed. They also offer both relaxation and excitement. These are larger than daysailers but still easy to handle.
• Catamarans: This multihull boat provides stability and speed while also remaining comfortable. This allows for swift travel and tons of room on the boat for large groups.
• Center Console Boats are versatile options for anyone that wants to go fishing and cruising. They are usually small enough to go exploring Chesapeake Bay's inlets and coves. They also provide excellent visibility and handling no matter your experience level.

Why You Should Sail in the Chesapeake Bay

Choosing to sail in the Bay could lead to an unforgettable opportunity. There is more than a day’s worth of things to do in any location that you choose.

Appealing Scenery

There are not too many locations that you can sail to that have a balance between urban or city life and sailing. You will be able to see a lot more than people that do not have boats and the tours can only provide so much.

Calm Environment

Chesapeake Bay offers calm waters most of the time but checking the weather conditions is always best before making the trip. It does not matter if you are a first time boat owner or experienced sailor the weather will impact your performance. Thankfully the Bay has dependable weather.

Exciting Opportunities

Whether it is your first time sailing or you are visiting again the Bay offers endless opportunities. These could be fishing or crabbing and maybe even a new restaurant to try out. All of the locations have different historical aspects as well.

Best Memories

In combination of taking the opportunity to explore you will be making some of the best sailing memories. There is a reason why Annapolis is the center for sailing and the Bay is a perfect representation that offers the perfect package.

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I've personally had thousands of questions about sailing and sailboats over the years. As I learn and experience sailing, and the community, I share the answers that work and make sense to me, here on Life of Sailing.

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Boats of the Chesapeake Bay

The Chesapeake Bay is home to a diverse cast of boats, many of which are so unique to the area that you won’t find them in any other region. For centuries, different vessels have been invented to suit the needs of fisherman, explorers, athletes, scientists and anyone else taking to the water on a regular basis. Though some might be remnants of a bygone era, these 11 iconic watercraft have sealed themselves into the culture and history of the Chesapeake.

Recognized as the Bay’s first workboat, log canoes once filled the estuary as watermen sailed about in search of fish and shellfish. They are usually made from three to five hollowed out logs that are fastened together and shaped into a hull—a simple but effective design based on similar boats built by the Powhatan Indians . One or two large masts jut out from the center of the boat, and sails capture the wind and use it as a propellant. Most log canoes that exist today have been retired from their working lives and are instead sailed in novelty races.

In the early 1800s, oyster dredging was banned in the Bay, so oystermen relied on log canoes to navigate the waters and used oyster tongs to snag the popular bivalve . When bans began to lift, a new type of boat was needed to be powerful enough to haul a dredge but lean enough to navigate shallow waters where oysters are found. Thus spawned the bugeye, a unique Chesapeake Bay invention used in early oyster dredging until it was replaced by the cheaper, but just as effective, skipjack.

In the late 19th century, the skipjack—a popular work boat for watermen—saw a production boom as the Maryland oyster harvest reached an all-time peak of 15 million bushels. But as the Bay’s oyster population steadily declined, so did its skipjack fleet. There are 35 skipjacks left in the Bay region, many of them used for educational purposes (like the Chesapeake Bay Foundation’s skipjack, Stanley Norman ). The skipjack is as unique a Chesapeake boat as you’ll find—so much so that the state of Maryland named the skipjack its official state boat in 1985. All throughout Maryland’s Eastern Shore, you’ll find skipjack races being held.

Skiffs are shallow, flat-bottomed boats recognizable by their sharp bow and square stern. These watercraft are made to move through tight tributaries and along the coastal areas of the Bay. While they can be used as workboats, skiffs are typically used for recreational fishing and other leisurely outings.

The official boat of Virginia, the deadrise is a traditional work boat used by watermen to catch blue crabs , fish and oysters. The vessel is marked by a sharp bow that expands down the hull into a large V shape and a square stern. This was developed to help the boat navigate the Chesapeake’s choppy waters. The deadrise is said to be an evolution of the skipjack, and at times is considered something of an ugly but effective sibling .

Research vessel

Restoring an ecosystem as complex as the one in the Bay watershed requires constant monitoring and assessment. Research vessels like the University of Maryland Center for Environmental Science’s ( UMCES ) R/V Rachel Carson travels around the Bay collecting data on water quality, flora and fauna to help scientists gain a better understanding about how to improve restoration efforts. The vessel can support up to 28 people, including crew for daily operations, while 13 people can be accommodated for multi-day excursions.

Schooners are sailing ships with two or more masts. They have a long history in the mid-Atlantic as workboats for the watermen who made their living harvesting oysters, blue crabs and fish from the Bay. In October, schooners can be seen racing 146 miles down the Bay from Annapolis, Maryland, to Hampton Roads, Virginia, as a part of the Great Chesapeake Bay Schooner Race . This race was started to draw attention to the Bay’s heritage and to support environmental education and restoration work.

Racing shell

The sport of rowing, often referred to as crew, is a popular pastime for many who live in the watershed. Rowing clubs such as the Eastern Shore Community Rowers , Chester River Rowing Club and the Central PA Rowing Association all exist in the watershed, while many of the region’s colleges and universities support competitive crew teams. While racing, athletes sit with their backs to the bow of the racing shell and face the stern, using oars to propel the boat forward in one unified team.

The shipping industry has been critical to the mid-Atlantic economy since the colonial era when the region first started serving as a bridge between the northern and southern United States. In fact, the Bay is home to two of the country’s five major North Atlantic ports: Baltimore, Maryland, and Hampton Roads, Virginia. Cargo ships were created to transport large amounts of commodities and can range in size and capacity from several hundred tons to several hundred thousand tons.

You’d be hard pressed to find any buyboats out on the water today, but there was a time when you couldn’t toss an oyster shell without hitting one. Like the same suggests, buyboats were used to sail out on the water, buy oysters from watermen in the wintertime, and haul them back to shore to sell. During the summer, they were used to haul all kinds of heavy materials used by watermen and merchants.

Menhaden steam ships

Menhaden steam ships have a complicated history. Before we knew how endangered and important to the food chain menhaden were, fishermen harvested them relentlessly, making the menhaden steam ships they piloted a well-known vessel. These ships are no longer used but are fondly remembered by many in the Chesapeake region for their bombastic appearance and the great plumes of smoke that marked their presence.

Want to learn more about the Chesapeake Bay? Visit our History page to read all about the region’s earliest inhabitants.

Virginia's Government still doesn't understand (or care) about the importance of Menhaden to the Chesapeake Bay ecosystem.

Might want to include the bay steamers that ran up and down the bay and up the creeks and rivers. The transportation backbone of the region for more than a century. And don't forget all the ferries either!

Can anyone give me information on Artist George Wendt who drew these beautiful Chesapeake Bay Workboats in pen and ink in the 1970, s ? I have A collection of 4 and would like to know about the artist! Thank you !

Not all deadrises have square sterns. Many have the lovely round stern, and a few of the older girls still have the classic Diamond Stern. And you forgot the gorgeous Hooper Island Draketails.

Hey Joseph, you have a sharp eye! We replaced the photo skiff photo. Thanks.

If you look closely, that's a CAROLINA SKIFF, which is a flat bottomed, fiberglass scow. A real Chesapeake Bay skiff was built of qood, with a pointed bow, and most often a flat bottom, but they were also built as a modified deadrise.

I was very surprised that the Bugeye was not mentioned at all.

Seriously? You describe skiffs as flat-bottom boats and show a picture of a round-hulled boat. But worse, you talk about schooners on the Chesapeake Bay and show a picture of Alma, a scow schooner that only ever sailed on the San Francisco Bay and some tributaries. That's 2,500 miles away from the Chesapeake. Surely you can do better than this!

Yes dont forget the Buyboats and Dont forget about the Pungy Schooners..They were small, bay - built 1 to 2 masted schooners with flush decks, low sides and deep draft with big round bilge bellies for hauling cargo offshore , up and down the coast and to Baltimore from Bermuda ..They used to haul fruit from Bermuda back when one had to get fresh fruit or not get it at all... The big cargo freighters didn't bother with the short run to Bermuda to get fruit..they cost too much to operate so they had to get paid more for long hauls of more expensive cargos..They left the Bermuda runs to the little "bannana boats" , the Pungy boats..There are no authentic Pungy's left afloat, but the "Lady Maryland" is thought to be an accurate replica. Some clever wood boat builder ought to make a yacht version or two. Good luck finding the drawings for one , although one drawing does exist..A boat commissioned in Virginia in about 1850..

Very nice! Dont forget about the old Buy Boats and Menhaden Steam Ships.

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Chesapeake Bay Magazine

The Best of the Bay

Boats Not to Miss

When it’s boat show season, the selection of new boats to check out is vast, and every shiny, white hull on the labyrinth of docks starts to look pretty good. Chesapeake Bay Magazine is always happy to round up the best of the year’s debuts. This year, there’s no labyrinth of docks to get lost in, sadly, but that’s why we’re here to bring you the best of the new. Our top picks for new boats are multi-function vessels that pack a punch.

To design the Sun Odyssey 410, Jeanneau reached out to long-standing design partner Marc Lombard , who was assisted by Jean-Marc Piaton. Together, they delivered on the challenge of bringing the classic Jeanneau styling into a modern yacht. Like the 440 and 490, the Sun Odyssey 410 features a generous beam and walk-around deck, ensuring life on deck is comfortable and spacious, either under way or at anchor. Simple sail handling is ensured through an integrated bowsprit, inboard winches, and recessed wells for controls.

The Lombard-designed, hard chine hull combined with a high aspect cathedral rig, add to its performance. The fine entry wave-piercing bow significantly reduces drag, while giving the boat a distinctive look. In addition, careful consideration has been put into weight distribution and balance in the sail plan, bringing a new level of performance to the Sun Odyssey line. Even the most competitive sailor will love the speed, responsiveness, and ease of handling while at the wheel. Available from Crusader Yacht Sales in Annapolis.

The exceptional new F45 flybridge delivers unparalleled space, quality and flexibility for the ultimate on-water experience. Its extended flybridge includes a seating area with teak dining table and forward L-shaped seats that convert to a sunpad when required. At the touch of a button, the unique, electrically-sliding transom seating arrangement extends the length of the cockpit area to deliver notable main deck space for a 45-foot yacht. Below deck, a full beam owner’s cabin complemented by a forward ensuite cabin await. Powered by Volvo IPS 600’s and reaching a top speed of 31 knots, the F45 is both powerful and beautiful. With elegant full-length hull windows and unusual design detail, the F45 is set apart among small flybridge yachts. Available from Bluewater Yacht Sales , with nine locations along the East Coast and a brand new full-service sales and repair facility in downtown Annapolis.

Start planning for summer fun with the Grady-White 30-foot dual console, the Freedom 307. Perfectly suited for the family that wants the flexibility to do it all, this boat’s design was derived from customer requests for a roomy cruiser with Grady-White’s heritage of fishing features, rich amenities and exceptional performance. You’ll find no boat more luxurious in its size and class.

Grady-White thought of every comfort when they designed this elegantly rugged, reliable boat. From the expansive console with head, sink and bulk storage to the roomy cockpit with wet bar, optional grill and refrigerator, this is an excellent choice for the family looking for a well-appointed boat that’s suited for a variety of coastal waters—all on the industry’s best-riding hull, the SeaV2®. Grady-White’s Freedom 307 is an evolutionary step up in recreational boating and sure to make all your summers memorable. Available from Tri-State Marine and Taylor Marine.

For decades, the Boston Whaler Dauntless series has led the industry in confident performance and multitasking capabilities. The tradition carries into the future with the 220 and 250 Dauntless. Each model combines inshore fishing excellence with offshore cruising comfort. Much more than an average bay boat, the 250 provides a spacious layout with plenty of seating and smart amenities for fishing, watersports and cruising. The 250’s inviting bow lounge has folding backrests and lockable storage and room for 7-foot rods. The head has an enlarged door for easier access, and the new fold-up stern deck seating area complements a sleek, redesigned hull. Available from Chesapeake Whalertowne .

Constructed with many of the high-quality materials found in larger models, this craft offers stunning good looks on a super-durable Vinyl-Ester Epoxy Resin hull that is foam filled and resin sealed to render the Cuddy safe and virtually unsinkable. A precisely balanced, variable-deadrise hull is stable at rest yet dry and comfortable in chop. This hull design produces much greater performance with less horsepower than other 23-foot boats. The savings in power package costs allows for the finest components and materials during the construction process without breaking the bank. With seating for eight, modest sleeping accommodations below deck, and a head in the cabin, a fun day on the water can be extended overnight. There is a wide range of options that encourages each owner to put their unique signature on a cuddy cabin that turns heads at every port. Available from Annapolis Yacht Sales .

The Legacy Series comes loaded with incredible standard features as well as a wide range of options, and the 2302’s rugged hull is up to any challenge brought by avid sportsmen and recreational boaters alike. High, flared sides ensure a dry ride for everyone on board. The helm holds a wide station with room for two chartplotters, a deluxe leaning post, and rod management with storage for up to 10 rods. At the transom, three-across seating doubles as livewell and storage. The 2302 Legacy’s stable, wide fishing deck is easily converted to a picnic area, and bow seating features include back rests that fold flush with the gunnel when the fish start to tug the lines. The staunch 2302 Legacy will get you to fish your best—and bring friends and family to the game. Available from Port Annapolis Marina .

The new R-41 from Ranger Tugs is as luxurious and comfortable as it is strong and seaworthy. With two private staterooms, each with en suite head and shower, there’s plenty of room to comfortably entertain guests. The R-41 is packed full of innovative new features that will make your life on the water stress free and fun. Designed and built by hand in the USA, the R-41 will turn heads and collect fans everywhere you go. You’ll love the massive cockpit, with transom seats that rotate open to present a pass-through to the oversized swim step. Abundant seating, ice maker, sink and a joystick docking station can also be found in the cockpit. The spacious, light-filled salon is the heart of the R-41. With a conversational layout and seating for 12, you’ll make a lifetime’s worth of memories with friends and family in this warm, inviting space. Available from Pocket Yacht Company .

The latest in Bayliner’s VR Series of highly evolved bowriders, the VR4 is easy to tow, launch and store—and really fun to use. The smallest VR Series model delivers plenty of interior space thanks to the BeamForward™ design, which carries the full beam further forward for more comfort and capacity than traditional pointed bows. Our AftAdvantage™ design increases the rear seating area by shifting it to the aft-most point of the running surface, allowing the swim platform to extend beyond that. That means more room for comforts like movable backrests for versatile seating configurations, available bow wind block and optional filler cushion that together create an additional bow seat, optional sun pad cushion inserts that expand the sunbathing area, and plenty of convenient storage throughout. Available from Riverside Marine in Essex, Md.

Common sense, time-tested design and a straightforward approach, combined with the uncompromising dedication to quality construction practices, has earned the entire Parker line the reputation of strength, simplicity, and seaworthiness. All Parker boats are hand-laid from the finest roll stocks and resins available. Deck hardware is thru-bolted stainless steel with backing plates. 

The tradition continues with the 2100 SE. Whether inshore fishing, offshore trolling, or enjoying water sports with the family, the 2100 SE checks all the boxes in an efficient and affordable package. Parker’s Special Edition (SE) center consoles offers Mod-V hulls and forward platforms for additional seating or casting to provide flexibility for both inshore and offshore use. The Deep-V, with its sharp entry and wide beam, is ready to handle sporty and extreme offshore conditions with ease.

From big seas to shallow creeks, the Parker 2100 SE has the flexibility, strength, and seaworthiness to get you to your destination safely and comfortably. Available from Tri-State Marine .

The Pursuit S 328 broadens the range of Pursuit’s popular Sport Series. The athletic exterior is complemented by a forward wrap-around lounge at the bow, just opposite of the forward-facing seating in the console, to create a nice place to socialize.

Below is a two-person berth, head, and sink with vanity that could let you overnight and freshen up for a dinner shore side. The aft cockpit accommodates serious fishing and, with its fold-away fore and aft seats, quickly converts to a social area at the dock. Available at North Point Yacht Sales and Bosun’s Marine .

Boston Whaler calls their new 240 Vantage a Swiss Army knife for boating. A true “do-it-all” platform, the 240 is designed to deliver remarkable versatility and comfort. With an array of features for fishing, cruising, beaching, watersports and entertaining, this dual-console model is perfect for active families eager to enjoy everything possible on the water. Powered by a V8 Mercury Verado engine, this design features a flared hull and sharper bow profile to provide a stable, safe and seaworthy ride. Dealers on the Bay include Chesapeake Whalertowne , Taylor Marine Center , and Lynnhaven Marine .

Edgewater’s new center-console premiered late last year. This boat is chock-full of standard features and options that are top-notch for the family and angler alike. It can rip through the blue with its optional engine setup of twin Yamaha XTO 425hp. The optional Seakeeper can keep her even steadier in choppy conditions. The console head has plenty of storage and an impressive amount of room. There is a leaning post with an aquarium livewell and tackle drawers, but also a classy Corian countertop and cutting board. And the family will appreciate its plush forward sun pad lounge seat and dinners around the easy-to-use, stowaway bow table. It’s sold on the Chesapeake by Annapolis Yacht Sales . 

This robust little smart cruiser looks unashamedly like a small yacht. With its slender bow, optimized weight, and square-top mainsail, it performs well in all points of sail. For beginners or for short-handed sailing, the self-tacking jib and the single winch are easy to handle. For performance, the Oceanis 30.1 has a large overlapping genoa, a furling code zero and an asymmetric spinnaker. Aft, a step affords access to the water and can be supplemented by a small lifting platform. The cabin has 6.5 feet of headroom and two sizable double cabins each with berths running lengthwise and an open entryway making them feel particularly spacious. The two benches in the salon provide two extra berths. With unbeatable living space for its size and a focus on simplicity of use, the smallest model of the Beneteau cruising range is stylish and fast, with a highly competitive ready-to-sail price. The Chesapeake dealer is Annapolis Yacht Sales . 

Ranger Tugs’ R-25 is a feature-packed cruiser designed for comfort, ease of use, quality and fun, says the manufacturer. For over 60 years Ranger Tugs has been building boats, so the R-25 combines a wealth of experience gained over many years with modern design and technology, to provide the best in handling, seakeeping, and performance. Powered by a single Yamaha 250hp Outboard driving a modern hull, the boat is fast and efficient whether planing or running at displacement speeds. The R-25 is sold ready-to-cruise, meaning it is packed with standard features like a bow thruster, inverter, battery charger, solar panel, shore power with 30-amp chord, raw water washdown system, electric marine head with holding tank, deck outlet and macerator, anchor, chain and rode, a windlass with bow and helm controls, a cockpit Bimini top and more. It’s quite a platform for a 25-footer. The Bay dealer for both Ranger Tugs and Cutwater is Pocket Yachts .

The first in its series, the 43LE emphasizes the brand tenets Tiara Sport has become famous for: sport styling combined with luxurious amenities, dedicated social zones, and thrilling performance. A large chaise lounge on the bow provides relaxation, while the signature rotating lounge seats in the aft cockpit (complete with multiple locking positions and built-in footrests) allow guests the flexibility to face forward, astern, or sideways toward the fold-down terrace. Premium entertainment features are found throughout and below deck along with two sleeping accommodations: a queen island berth and a mid-cabin double berth. A complete head with separate shower provides all of the appropriate overnighting or day-yachting amenities. With two unique propulsion options (Mercury or Yamaha) and an integrated electronics package with Garmin Marine Navigation systems, the Tiara Sport 43LE is built for performance, comfort, and ease of use. The Chesapeake Bay dealer is North Point Yacht Sales .

This is the smallest large-scale production cruising catamaran on the market, but don’t let its size fool you. The Excess 11 offers the comfort and space of a much larger boat, as well as thrilling performance and amenities that make it capable of long passages and life onboard. The work of its naval architects and designers has been focused on one objective: to create a real cruising catamaran in a smaller package with volume worthy of a larger boat, whether in the saloon or in the cabins. For example, the owner’s berth has a large 6.5 x 6.5-foot bed and each bathroom has a separate shower. On deck, it offers the comfort and friendliness of a large open cockpit and twin helm stations, allowing for real steering sensations as well as direct contact with the rest of the crew. This is the synthesis of the Excess spirit: a beautiful, simple, light and comfortable boat, capable of taking you to the most remote spots on earth. The Chesapeake Bay dealer is Crusader Yacht Sales .

An exceptional 33-foot center console, Grady-White’s Canyon 336 provides the best of everything you’d expect, and more, in a boat of its size. The 336 starts with superior quality, reliability, safety, performance and long-lasting value Grady-White is known for. Its sleek styling elements are elegant, while abundant bells and whistles make it a well-outfitted fishing machine. Already a strong seller in this market, the new changes are bringing high demand. The redesigned console and T-top, with fully integrated windshield, widens walkways and expands the cockpit and bow spaces. An all-new helm design includes room for dual 17” flush mount electronic panels strategically located closer to the captain. From bow thruster and Yamaha “Helm Master EX” Digital Electric Steering to a water heater, air conditioner and diesel generator, the Canyon 336 is a high-performance boat that doesn’t compromise Grady-White quality and comfort. All built on Grady’s exclusive “SeaV 2” hull, it delivers a dry, soft ride.

Is this boat designed for the serious angler or the family? We think both. The Open 282 by Sportsman is a great all-around boat that provides creature comforts for entertaining with family and friends and a sturdy, dry, and fast ride so you can compete offshore with the big guys. Enjoy the electronically actuated bow table that easily adjusts into three positions, from tabletop to sun pad to flush with the floor. The side-entry door makes dockside loading (of kids or fish) a breeze, and quickly becomes a feature you cannot live without. This boat comes loaded with many standard features, like the oversized hard top with lights, speakers, and more. Yacht Certified and therefore exempt from required vessel capacity limits, the Open 282 provides a safe and comfortable ride for the entire family. A pair of Yamaha 300hp outboards puts you at your destination quickly, and if you’re into bells and whistles, make sure you check out the Tournament Edition. You’ll find a video review of it here . The Chesapeake Bay dealer is Riverside Marine .

Better Sailing

Best Sailing Destinations in Chesapeake Bay

Few places on Earth are as easy and beautiful to sail as the Chesapeake Bay, with its rich maritime history, attractive villages, and innumerable bays, creeks, and anchorages. It’s no secret that Annapolis, MD is America’s Sailing Capital, and it’s home to some of the top sailing spots in the country. The Chesapeake is a body of water that stretches 200 miles from the mouth of the Susquehanna River in Havre de Grace to the Virginia twin capes. It varies from 3 miles wide in the north to 25 miles wide in the south. Its lowest point is 200 feet south of Bloody Point on Kent Islan, despite being notoriously shallow in some of its finest streams and bays. It’s important to note that weather and navigational conditions vary greatly in the Chesapeake Bay. Now, keep reading in order to learn more about the best sailing destinations along the Bay!

Baltimore, Maryland

The Patapsco River empties into Baltimore’s Historic Inner Harbor. The Inner Harbor is a fantastic place to start sailing because it has a lot of marinas. In the Harbor, you can see historic Federal Hill and Fort McHenry, and when the Patapsco opens up into the bay, you’ll find other outdoor attractions including North Point State Park and Fort Smallwood Park. The true city on the northern bay, Baltimore is a must-see when sailing there. Henderson’s Wharf Marina, located in the center of Fells Point, has a great anchorage.

You’re nearby to many of Baltimore’s top pubs, taverns, and music venues. Consider sailing to Smith Island, Worton Creek, and Island Pond, find an anchorage, and relax aboard. In fact, the unlimited possibilities are what you will enjoy most about this body of water. But, note that despite all of the sailing and racing many people do there, they feel like they’ve merely scratched the surface.

Galesville, Maryland

Galesville is a small town on the west bank of the bay situated along the West River. This lovely town used to have a steamship line that ran between Annapolis and Baltimore, and it was previously home to numerous Chesapeake Bay watermen. The West River Sailing Club and Hartge Yacht Harbor are now located there, making it a popular site for leisure boating. Galesville is located at the end of Route 255, which becomes Galesville Road and then Main Street as you travel deeper onto the little peninsula. Main Street comes to an end at the water’s edge, where there is a small community park with a 14-mile boardwalk along Riverside Drive on the West River.

Wye River, Maryland

This is one of the most tranquil and bucolic places in the Bay. When sailing there, the place will instantly make you forget the city life. The Wye is a 16-mile-long tributary that surrounds Wye Island, a 2,800-acre nature preserve. Wye Island, on the Miles River’s northern shore, is home to bald eagles and great blue herons. It also features “Schoolhouse Woods,” the Eastern Shore’s biggest intact stretch of old-growth forest. The Wye also has several additional magnificent protected creeks and bays where you may drop a line and find your own little heaven. It’s advisable to take your dinghy and go exploring. Along the island’s lonely shoreline, there’s an almost infinite supply of isolated picnic-perfect beaches.

Solomons Island, Maryland

Solomons Island, located at the mouth of the Patuxent River, was home to multiple 19th-century shipyards that supported the local fishing industry. Many marinas, seafood restaurants, the Calvert Marine Museum, and the Annmarie Sculpture Garden & Arts Center are on Solomons Island today. Its riverside location makes it a popular cruising destination. At the confluence of the Bay and the Patuxent River, Solomons Island is a small, working fishing town. Solomons Island has quickly become a favorite among sailors due to its abundance of activities. Calvert Cliffs and the Drum Point Screwpile Lighthouse offer fantastic restaurants and stores, as well as fossil collecting. To get the most out of your voyage, set aside two days, stopping in Harrington Harbor on the way down and St. Michaels on the way back.

Potomac River

Bay cruisers know Solomons is a beautiful destination with excellent marinas, restaurants, and a fantastic maritime museum, as well as a suitable staging place for crossing the Potomac. It’s about 40 miles south of Solomons to the next harbor, either Reedville or Tangier. When the wind resists the current at the mouths of the rivers in the Chesapeake, the water can become “lumpy.” When the current and wind is in opposition, the Potomac’s mouth should be acknowledged as the Bay’s major tributary. Ducking into Tangier Sound through Hoopers Strait or Kedges Strait and visiting the Eastern Shore will be a more comfortable trip in such conditions.

This route will take you to some of the most isolated and underdeveloped portions of the Lower Eastern Shore. You will also find innumerable lovely and secluded anchorages and several little villages worth seeing, such as Deale Island, Onancock, and Crisfield. The picturesque Pocomoke River, which makes its way through a cypress swamp, may be accessed from Crisfield. This is a truly magical location. There will be no noises of human activity if you turn off your engine.

Saint Michaels, Maryland

In St. Michaels, there are many marinas, a protected anchorage, a launch service, and great restaurants and pubs. The town is arguably one of the most attractive and popular on the bay. The Chesapeake Bay Maritime Museum is St. Michaels’ crown jewel. Many permanent displays at the museum illustrate the geological, social, and economic history of the Chesapeake Bay from the dawn of sail through the period of steam and diesel-powered ships. A great variety of vintage boats are always on display at the museum’s piers, and people are routinely invited onboard for short cruises on the Miles River. In addition, St. Michaels has seen a bit of a gastronomic explosion in recent years, and it now boasts some very good, fashionable new restaurants. For example, 208 Talbot is a terrific spot to go for a casual, relaxing supper in a pleasant setting.

Tilghman Creek, Maryland

If you can’t find a berth for the night after a long day sailing to St. Michaels, you might not want to push into the port. This is particularly true if you are not passing through Kent Narrows. Tilghman Creek is located on the Eastern Bay, just around the corner from Rich Neck. Claiborne is a little settlement at the head of the creek. There is a couple of workboats moored nearby. There are also a few houses along the creek. Despite the seeming availability of space, you should avoid anchoring near the creek itself to prevent interfering with the watermen who leave early in the morning.

Annapolis, Maryland

Annapolis, also known as the US Sailing Capital, is home to a number of boat shows, and the National Sailing Hall of Fame. Its location along the South River, Severn River, and the Chesapeake Bay make it an excellent sailing launch point. Annapolis is one of the bay’s most historic and well-preserved waterfront cities. You could spend days wandering here, with the beautiful Maryland Statehouse, the Governor’s Mansion, the classic and traditional Naval Academy, and the twisting lanes and old maritime mansions. Pussers Caribbean Grille, which overlooks Spa Creek, is one of the area’s traditional pubs. Note that you can rent a mooring ball in one of the marinas in Back Creek. Lastly, getting around Annapolis is not hard because there’s a water taxi service.

Delaware Bay, Delaware

Delaware City is located on the northern end of the Delaware Bay, about 1/2 mile north of the C&D Canal’s Eastern entrance. It is a small community that may be reached on foot from the Delaware City Marina. The Cohansey River is located just southeast of where the Delaware Bay meets the Delaware River. The river is a shallow salt marsh at the Bay entry to the Cohansey. As one moves upstream, the river gets increasingly forested. The salt marsh location has excellent anchoring in terms of water depth and swing space.

Philadelphia, the City of Brotherly Love, is roughly 35 NM east of the canal entry. The entrance to the Christina River and the Port of Wilmington is about 10 miles up the river. Lewes, a beautiful hamlet across the bay from the Cape May Canal, is only 12 miles away. At the bridge that spans the canal and goes to the beach, you will find the city dock. The west end of the Cape May Canal, where the Cape May-Lewes Ferry terminal is located, is where the approach to the harbor from Delaware Bay begins.

Note that before crossing Delaware Bay, you should carefully check the weather forecast. This vast, wide, and exposed body of water is located in the Southeast to Northwest direction. Don’t get me wrong: it’s a great ride in good weather. In this stretch, however, you just have to be cautious! It’s advisable to stay in port if the conditions seem unpleasant for sailing.

Deltaville, Virginia

The majority of the boats heading south from Solomons easily cross the Potomac, stopping in Reedville or Deltaville, Virginia. The rivers and creeks of Virginia’s Northern Neck lie between these two attractions. You’ll know you’re in the Southern Chesapeake whether you choose the larger waters of the Great Wicomico or the well-protected shelter of Mill Creek. Both hurricane holes and anchorages are open to summer breezes in Dividing Creek. Also, note that Hughlett Point State Park’s sandy beaches are accessible from this location.

Experienced Southern Bay sailors will tell you one thing about Stingray Point, which marks the southern end of the Rappahannock River’s entry. They’ll tell you to keep your depth and not wander too close to the mark at first. Expect nice marinas with amenities and maritime services in Deltaville, which is a bit more spread out than other towns with a charming center to meander through. Carter Creek is located on the far side of the Rappahannock River Bridge on the northern side of the river, sometimes known as the “northern neck.” The Chesapeake Restaurant & Terrace offers a unique touch on coastal cuisine for casual dining.

Tangier Island, Virginia

Tangier Island is a must-see on any Southern Bay voyage. You will dock at Parks Marina in Tangier during your stay. Note that Tangier’s sole industry is seafood. For 350 years, the island’s economy has been based on crabbing, oystering, and fishing. Tangier Island’s main street, lined with crab shanties, many of which are built on stilts over the water, provides a view of the working Chesapeake that has vanished from almost every other harbor. The island is a significant soft crab provider. Tangier History Museum and Cultural Interpretive Center is the most prominent museum dedicated to the lives of Chesapeake Bay watermen.

Peter is the editor of Better Sailing. He has sailed for countless hours and has maintained his own boats and sailboats for years. After years of trial and error, he decided to start this website to share the knowledge.

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• 7 Towns In Maryland With The Best Downtown Areas In 2024

A seasoned vacationer will tell you that a town is as good as its downtown area. It does not matter if it has the best theme park in the world, a rich history, or a kick-ass dining scene. Maryland , one of the original thirteen colonies, is start-studded with an enchanting range of many beautiful towns, some of whose downtown areas look plucked straight out of a movie scene. Granted, many will cast their vote for Fredrick, a dreamy place that looks like a well-planned neighborhood more than it does a city. But the focus here is on slightly smaller towns. Here we go.

Transport your mind to charm-soaked streets, a quaint, historic waterfront, and a couple of 300-year-old buildings. Speaking of years, Annapolis was settled in 1649. Its settlement history, therefore, goes back more than 370 years. Start exploring Annapolis at the top of Main Street, preferably after a hearty breakfast at Miss Shirley's Cafe, whose dishes — which should feature blueberry pancakes — come with lots of yummy twists. Walk down the hill, taking it slow and light, until you reach City Dock, where you can relax on a bench that overlooks the beautiful harbor. One can easily lose all sense of time here, as the sumptuous views, sprinkled with the sight of cruising boats, can put one in a dreamy, trance-like state. Have a glimpse of the Maryland Statehouse, which is open to the public every day from 9.00 AM to 5.00 PM. We are talking about the oldest state capitol in continuous legislative use in the entire nation and the only one to have served as the nation's capital.

Westminster

Westminster has some interesting claims to fame, including being the site of the first rural free mail delivery in the United States. It was founded in 1764 and initially named Winchester after the founder. A frustrating confusion with Winchester, Virginia, however, forced the town's early settlers to rename the town for London's Westminster borough. A summer afternoon stroll can reveal much about Westminster’s downtown beauty. Westminster is a suburb of Baltimore, only about 30 miles stand between them. It boasts some really great restaurants, including Rafael's, Rock Salt, and O'Lordan's, which is set in a beautiful 19th-century stone building. The town's Main Street, with its beautiful shops and boutiques, is usually the main draw.

Carroll Arts Center, which locals love to bits, is a shining beacon of culture and community. With academic institutions such as the McDaniel College, the ambiance here is open, warm, and vibrant. Just don't miss Hoffman's Ice Cream, which serves the best homemade ice cream for miles.

Although Paris is known across the globe for its alluring thrifting scene, Berlin, a cute little town in Maryland, can make one for a moment think she is in the City of Light. Open Hand Thrift, for example, just outside Main Street, has almost everything, whether kitchenware or jewelry. But the inner core, with its tree-lined streets and Victorian charm, can also steal the show. No wonder Berlin's downtown is a National Register Historic District — and has served as the setting for many films, including Tuck Everlasting, an American romantic fantasy drama film that was released in 2002. With its many galleries and murals, Berlin’s art scene is not just alive but thriving. The Worcester County Arts Council, right in the heart of town, features unique, hand-crafted artwork, mostly from local artists. There is also Calvin B. Taylor House, an eye-catching Federal-style house that serves as a repository of local history. For something off-the-beaten-path, look no further than the Mermaid Museum. It is a fun, quirky distraction with a lot of information about the history of mermaids. Xxx

St. Michaels

Unless you have had the pleasure of experiencing it, you may find it hard to believe that St. Michaels has the most endearing Christmastime Main Street, not just in Maryland but also in the entire country. Granted, it is still magical January and June, but when the festive season knocks, it takes everything a notch higher. That said, its year-round features include kitschy nautical shops, a beautiful waterfront, cobblestones, historic homes, and a swoon-worthy setting on the Chesapeake Bay. The Wildset Hotel, with its eye-catching swimmers mural, has a history that dates back to the 19th century. Chesapeake Bay Maritime Museum offers a glimpse into the misty past — as is the Hooper Strait Lighthouse, loved for its interesting maritime artifacts and stories. But time also seems to stop along Talbot Street, a lovely stretch that almost looks like it did 50 years ago.

Catonsville

Although they are close to each other, don't ever be tempted to overlook Catonsville for Ellicott City, a mistake that many make. The truth is, Catonsville is a hidden gem — and that is knowing the phrase is often misused. This Maryland treasure is cool, charming, and highly walkable. It boasts a lot of cute shops and restaurants so that a downtown adventurer will not be spoilt for choice. The bare minimum of a good Downtown area can be a long list of items. A good toy store, however, should never miss out on the list. Better World Imaginarium, which is small but well-curated, is just such a place. Walking down Frederick Road, with its trees and beautiful architecture, can feel like strolling through a Norman Rockwell canvas. There is the Lurman Woodland Theater if one wants to catch a good show — and Patapsco State Park — for those who want to venture out into the Great outdoors.

Havre de Grace

Think of Annapolis but without the crowds. That is one of the best descriptions of Havre de Grace, a quiet and picturesque Maryland gem that reclines at the mouth of the Susquehanna River on the beautiful Chesapeake Bay . Expect gorgeous waterfront views, colorful murals, and a charming, revitalized downtown. Stroll through Harmer's Town Art Center's mural park, for instance, and chat with local artists as you admire their beautiful exhibits. Linger a bit at the still brand new Graw Alley Public Art Park, a living and evocative outdoor art space dedicated to teaching the history of the town. If into lighthouses, perhaps because of what they embody, Concord Point Lighthouse is just a heartbeat away. Just don't miss a stroll along the boardwalk.

Leonardtown

Leonardtown has a cool little downtown area, the only designated Arts and Entertainment district in Southern Maryland. It spots breathtaking waterways, beautiful streets and landscapes, and a delightful range of pleasure spots. The Old Jail Museum, which looks like a time capsule, retains its original upstairs cells where convicted prisoners were once segregated by gender and race. The Leonardtown Visitor Center, also at the site, can help with mapping out one’s itinerary and maxing out on the experience. A traditional breakfast at Ye Olde Towne Cafe, some sweet treats at Heritage Chocolates, and Port of Leonardtown Winery, the first of its kind in the county, should all feature on one's itinerary.

The Takeaway

Maryland is known for many things, including its rich and storied history. The home state of Edgar Allan Poe was among the original thirteen colonies. Many of its towns are old, predating American Independence by several decades. Annapolis, for example, was already a proper town when the delegates signed the Articles of Confederation. Yet some of these towns are not just old. They are also incredibly beautiful, with downtown areas that are charming, quaint, and beautifully preserved. These include gems such as Annapolis, Leonardtown, and Berlin.

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