sailboat cruises portland maine

Dump out your bucket list.

This is the adventure you’ve been looking for..

Windjamming is, quite literally, like nothing else on Earth. By turns exhilarating, relaxing, surprising, and nurturing, it’s like no other vacation you’ve ever experienced.

Wake up to the quiet solitude of Maine’s coast, find renewal in the wind and sun, and surprise yourself as you help steer the ship. Aboard our vessels, with itineraries tossed to the wind, our guests find both a spark of adventure and time to reflect.

Is there a sailor in your soul?

Welcome to the Maine Windjammer Association – the largest fleet of traditional tall ships in the Americas. Our iconic windjammers offer multi-day, all-inclusive, sailing adventure cruises in one of the most acclaimed cruising grounds in the world.

When you sail aboard a Maine Windjammer Association vessel, you can be sure that your hosts hold themselves to the highest standards of safety and quality. As your captain and guide they will treat you to honest, heartfelt Maine hospitality and personalized attention.  Explore our fleet and offerings to find your perfect cruise.

The Windjamming Experience

Simply put, windjamming is about reconnecting with our essential enjoyment of life. It’s about gorgeous scenery, human connection, soul-nourishing meals, and taking time for both adventure and reflection. Our playground is the sparkling sea and the spruce-clad granite islands that rise from it.

Whether you join us for a three-night cruise or a week, we promise you a total escape from the ordinary. Be prepared to get closer than you ever have before to breathtaking wildlife like eagles, seals and porpoises, to visit some of North America’s most spectacular coastal scenery, charming villages and unspoiled islands, and to savor the freshest, fire-cooked Downeast fare. With only 16-31 guests on our ships, you’ll experience the kind of honest, heartfelt hospitality that keeps our guests coming back year after year.

Welcome to the only place in the world where schooners play in abundance. Where steady breezes, glittering bays, and literally thousands of islands make Penobscot Bay one of the most revered cruising grounds on earth.

On our small ship cruises, we have complete liberty to explore secret anchorages, remote fishing villages, and charming gallery towns. Schooners have been an intrinsic part of the Maine Coast for centuries, and there is something very special about rounding the point and arriving at anchorage under sail. Come touch this culturally distinct, pristine and physically breathtaking part of America.

Explore by Schedule

Use our cruise finder below to explore sailing options that fit your schedule. If your dates are flexible, or you just want to learn more, visit our fleet page and each vessel’s website. Reservations can be made directly with the Windjammer of your choice. Have fun exploring! Whichever vessel you choose, you are sure to have the sailing adventure of a lifetime.

Find My Trip

Everything about our experience was impressive. I'm still trying to wrap my head around how three extraordinary meals (and late afternoon snack)s are prepared and served daily. One would think that short cuts in meal prep would be expected but no, everything is freshly prepared and just delicious!

Stay in the Know

With our monthly newsletter, you’ll receive tips and hints from folks who have sailed as well as information about the best dining and attractions the area has to offer, special packages, windjammer history, events, and more!

You can request a mailed or digital packet of brochures, or you can find individual ships’ brochures under each listing on the fleet page.

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Portland Schooner Co.

Step Aboard The Extraordinary. Sail with us on an authentic, wooden sail boat steeped in history – and have the experience of a lifetime. Our fleet of historic schooners and our new picnic-style lobster boat provide the perfect vantage point to enjoy Maine’s most beautiful sights and sounds.

Maine State Pier Portland, Maine 04101

P. (207) 766-2500

T. (877) 246-6637

From Portland Harbor through the pristine waters of Casco Bay and beyond, refresh your spirit with a two-hour sail and witness first-hand the forts, lighthouses, sea life and rugged coastline.

Pack a meal, bring your favorite wine or beer and sit back and relax as our courteous and professional crew share their knowledge of the sea, sailing and local history. Or, if you feel inspired, join them to hoist the sails or take a turn at the ship’s wheel.

All ages are welcome! Whether you’re nine years old or 99, sailing aboard our Maine schooners is a unique adventure.

Two-hour day sails, lighthouse cruises, special events and private charters are available.

Casco Bay Custom Charters

Embark on an unforgettable journey: customizable private boat charters & tours of casco bay, celebrating a decade on the water.

Experience Casco Bay’s Splendor with Our Private Boat Charters & Tours. 

At Casco Bay Custom Charters, we invite you to explore the captivating beauty of Maine from the unique vantage point of our classic wooden vessels. For the past decade, we’ve shared more than just boat tours. Our charters are personal introductions to the coastal landscapes, lighthouses, and culinary delights that define our region. 

With a focus on customization, each voyage with us is tailored to uncover the genuine essence of Casco Bay, enhanced by our commitment to exceptional service. Led by experienced crews passionate about sharing their knowledge and love for Maine, we ensure your journey is not only enjoyable but truly memorable.

SEARCH CHARTERS BY GROUP SIZE

Designed for exclusivity, our charters accommodate intimate groups of up to 6 guests or larger gatherings of 7-16. Our friendly captains and knowledgeable stewards ensure a personalized boating experience.

Small Groups aboard MONHEGAN

Intimate cruises for up to 6 on a vintage lobster boat

Learn More »

Large Groups aboard MARIE L

Classic coastal tours for up to 16

DINING CHARTERS

The best way to eat locally-sourced Maine cuisine is aboard our Dining Charters. Specialty menu dining charters, chef’s dinner sunset cruises, and bottomless mimosa brunch cruises available. Local catering and all-inclusive drink upgrades are available aboard EVERY Casco Bay Custom Charter!

Private Sunset Dinner Cruise

Small Groups (up to 6 guests) aboard MONHEGAN

Bottomless Mimosas & Croissant Brunch

Large Groups (7-16 guests) aboard MARIE L

ELOPE ON A PRIVATE ISLAND

Experience the magic of saying ‘I do’ on a private island with our Fortland Elopement Package. Escape to Fortland for an intimate, and unique wedding ceremony set against the backdrop of a stunning coastal landscape. An unforgettable way to share your vows and begin your new adventure in love

FORTLAND ISLAND ELOPEMENT PACKAGE

Unique, intimate wedding ceremonies on Fortland.

SAIL WITH GLEAM

For a limited-time, we’re partnering with GLEAM to offer sailing charters off the coast of Maine. GLEAM is a fully restored vintage 12 meter yacht that hosts up to 13 guests. Each captivating sailing excursion includes captain and crew for an effortless Maine summer sail.

GLEAM Private Sailing Charters

Sailing Excursions along Maine's Coast

CREATE YOUR OWN CUSTOM CHARTER

Tailor any of our curated tours and experiences for your group’s needs, from corporate bleisure to family-friendly outings and celebrations. Collaborate with our team to craft your perfect day, selecting from diverse food, beverage, and tour itinerary options. Your bespoke Maine adventure awaits.

Unforgettable 5-Star Maine Experiences ⭐⭐⭐⭐⭐

Embrace authentic maine with casco bay custom charters.

Journey with us and unlock the essence of Maine on our signature boat tours. Enjoy the serenity of coastal cruises while indulging in gourmet locally-sourced food and craft beverages. Our classic wooden vessels offer a truly authentic Maine experience for unforgettable memories.

Eager for an unparalleled experience? Book your private boat charters and coastal tours to navigate the beautiful waters of Casco Bay!

Portland, Maine Historic Fort & Lighthouse Tours

Family friendly civil war fort tours, maine’s iconic lighthouses tour, and 21+ sunset cruises. a local craft beer, canned cocktail, or wine is included for every guest.

• Most Popular!
• Hour Glass 2 Hours
• User All Ages

Fort Tour on a Private Island

Casco Bay’s stone fortresses are captivating characters in the story of Maine history. For the first time, SeaPortland is bringing you to the historic site Fort Scammel via the Elizabeth Grace . Join us for a boat tour no other Portland harbor tour company can offer.    

• Hour Glass 1.5 Hours

Sunset Lighthouse Harbor Cruise

 There is nothing quite like a Maine sunset, especially from the water . Aboard the Elizabeth Grace , with local craft beers in hand, we will take you on a stunning journey through the waters of Casco Bay. Don’t miss this tour!

Scenic Lighthouse Harbor Tour

This epic tour is the best way to take in the historic lighthouses, stone forts, and rocky islands that make Casco Bay a world-renowned destination.

Limited Edition Tour

• Limited Time - Monthly Tour

Maine Island Rum Tasting and Boat Tour

Embark on a one-of-a-kind rum tasting adventure with Sea Portland and Three of Strong Spirits. Cruise Casco Bay to House Island aboard the Elizabeth Grace for a 90-min journey through Portland’ Maine’s candid history with prohibition and rum.

SeaPortland brings you straight into the heart of authentic Maine.

Aboard the Elizabeth Grace and other vessels in our fleet, we show you the parts of Casco Bay unseen by most. We provide experiences that strike at the heart of what makes this part of the world so magical.

Join us for boat tours of previously unexplored early nineteenth-century forts. Bathe in the warm lights of a summer sunset over the water. Breathe in the ocean air while viewing Maine’s famous lighthouses. Toast local craft beverages. What could be better?

Join us for a tour today.

• Chevron down Is there a head (bathroom) on the boat?

There is no bathroom on the boat. We highly recommend using the facilities before boarding. If you are on the Private Island Fort Tour there is a bathroom on the island.

• Chevron down Can I purchase more drinks on the boat?

Yes! Every SeaPortland tour includes 1 canned alcoholic beverage per person (local beer, hard seltzer, wine, canned cocktails). We have complimentary non-alcoholic beverages stocked aboard.

Following the first included beverage, additional beverages can be purchased via credit / debit card on the boat.

• Chevron down Should I tip the crew?

Yes. The boat crew is there to help keep you safe and to tell you about the sights in the harbor. They work hard to make it a great experience! The crew will split tips and for those wondering 20% is the common amount.

• Chevron down Can we bring our own alcohol on board?

No, we have our own license that prohibits guests from bringing their own alcohol on the boat.

• Chevron down Can we bring food on board?

Yes, feel free to bring food on board. We just ask that you also take any trash away with you as well.

• Chevron down Do we have to be 21 to take a tour?

Both our Sunset Tour and Rum Tasting Cruise are 21+.

Our daytime Lighthouse Tour and morning Fort Scammel Tour are for all ages!

• Chevron down What should I wear?

Dress appropriately for the weather. We will have a canopy which will protect you from direct sunlight and rain, however it can be significantly cooler out on the water so we recommend bringing a jacket. On the Fort Tour we highly encourage closed toed shoes.

• Chevron down What is your Cancellation Policy?

All ticket sales are final without Ticket Protection.

Tours cannot be exchanged, rescheduled, or refunded.

Ticket Protection allows you to cancel or reschedule your tour with at least 24 hours’ notice. We will reschedule or reimburse you for your full tour ticket price (minus booking and ticket protection fees).

We operate rain and shine as long as the waters are safe and we have met our minimum number of guests to operate the tour

Sailing in Portland Maine 

 Open Water Adventure

Come sailing on Mercury

Relax, listen to the water and enjoy the view

This is Mercury

2016 OVNI (Spacecraft in French) 395 constructed in  Aluminum

Mercury and I have sailed from France around the  Mediterranean and across the Atlantic. We have spent two seasons in the Caribbean and summer of 2023 will be on the East Coast. We are now doing charters in Portland Maine and Greenwich CT. Capt. is USCG qualified with over 16,000 miles under our keel ( actually a centerboard).

Our Cruises

Afternoon Cruise in Portland Maine for 4

Up to 4 people, only your party will be on the boat, just relax or ta...

Sunset Cruise in Portland Maine for 4

Online Meeting

What would you like to do today.

Go on one of our standard cruises or something else?

Captain Rick and Mercury have sailed around Europe, across the Atlantic and in the  Caribbean.

Custom Cruise?

Special Event?

Would you like to learn about the features of Mercury?

Buying a sailing boat for a long voyage?

Planning and preparing for a long sailing voyage?

Living full time on a boat?

Explore, Discover The Ocean

NorthPoint Yacht Charters arranges sailing and power boat cruising charters in Maine and Northern New England.

• Charter Gallery

Enjoy The Ocean With Your Family

NorthPoint Yacht Charters offers a wide variety of boats owned and managed by individual owners including both power and sailboats from 28-80 feet.

• How To Charter

Charter with NorthPoint Yacht Charters

Both bareboat and crewed charters are available. We also offer transportation, concierge services, bed and breakfasts, custom itineraries, provisioning, catering as well as special events. We are proud of our boats and take the extra time to make sure that your cruise will be pleasurable and trouble free.

About NorthPoint Yacht Charters

Welcome to the 2024 Charter Season

NorthPoint Yacht Charters arranges sailing and power boat cruising charters in Maine, Northern New England and the Canadian Maritimes. We offer a wide variety of boats owned and managed by individual owners including both power and sailboats from 28-80 feet.

Both bareboat and crewed charters are available. We also offer transportation, concierge services, bed and breakfasts, custom itineraries, provisioning, catering as well as special events.  We are proud of our boats and take the extra time to make sure that your cruise will be pleasurable and trouble free. 

Announcements

Luxury yachts.

Select from wide variety of boats including both power and sailboats 20-80 feet:

View Gallery

Osprey Hinckley Pilot 35 36‘

Lucky Dog Sabre 36 36‘

Thira Catalina 30 30‘

Curve of Time Morris Ocean 32 32‘

TIMELESS Offshore Motor Yacht 62 62' 62‘

from $28,500 /wk

Andromeda Sabre 30 30‘

Elan J-40 40‘

Sweetness Cape Dory 36 36‘

View Full Charter Gallery

What Customers are Saying...

KOAN performed beautifully. …. The engine runs great . MC

Our charter of Blue Goose two was excellent. She is the only boat I have ever charter or used including my own that there was nothing to fix. She was very clean, well outfitted with towels, linens and basic condiments.

We had a great cruise on Alliance. We visited Pulpit, Castine, NE Harbor, Seal Harbor (Vinalhaven), Islesboro and Tenants. RE

Get In Touch With Us

NorthPoint Yacht Charters arranges sailing and power boat cruising charters, we offer a wide variety of boats owned and managed by individual owners including both power and sailboats from 28-80 feet.

• Crewed Charters
• Experience Resume
• Charter Resouces
• Charter FAQs

We hope to see you in 2025!

Nautilus Sailing Company is closed for the 2024 season.

With great regret, we must close the 2024 season on a sad note.

The Nautilus was damaged by another vessel while at the marina in her slip, and is unable to sail. We hope more than anything to be sailing with you on the water again in 2025.

Until then, far winds and following seas on all your journeys.

--Sam and Crow, owners.

If Nautilus has provided you or loved ones with good memories on the water, or if you haven't yet been aboard and nonetheless generously wish to support us during this time, we have a GoFundMe running in an attempt to cover a portion of the repair costs to get this gorgeous boat sailing again next year.  

https://www.gofundme.com/f/help-sam-and-crow-keep-the-nautilus-sailing

Relax and enjoy the best views of Portland aboard Nautilus

Grab your favorite bottle of wine and step aboard for an experience you'll always remember. Sail past lighthouses, the historic Fort Gorges, and learn about the rich history of Portland Harbor from our seasoned and passionate crew.

Sail on Casco Bay with us!

Book a sailing adventure for a day trip, sunset cruise or your own private charter in Portland, Maine!

DAY SAILS &

PRIVATE CHARTERS

11:00 AM - 1:00 PM | Morning Sail

3:00 PM - 5:00 PM | Afternoon Sail

$80 per Person | $450 Private Charter

Hop on one of our 2-hour morning or afternoon sails to explore Maine’s diverse and scenic Portland Harbor.

Choose our first trip for a calm morning outing, or join us in the afternoon when the wind picks up. Get on the water with Nautilus Sailing Company for a uniquely memorable Portland, Maine excursion.

SUNSET SAILS & PRIVATE CHARTERS

6:00 - 8:00 PM | Sunset Sail

Fall Hours May Vary

$95 per Person | $550 Private Charter

Sunset sails depart each evening for 2 hours to enjoy golden hour views of Maine’s diverse and scenic Portland Harbor.

Bring your camera and favorite cocktail and get on the water with Nautilus Sailing Company to enjoy the best sunset views of Portland, Maine.

CUSTOM CHARTERS

Starting at $450 |  Call for a Quote

Need an extra hour or some additional flexibility? From intimate wedding ceremonies, to memorable anniversary celebrations, to unique bachelor and bachelorette parties, to corporate outings, our custom private charters are fully customizable to meet your needs.

Call to plan your ideal Portland Harbor sail charter and make your next special event epic!

BOOKING CALENDAR

Have a date in mind? View our Booking Calendar below:

Designed and built to look and feel like the sailing vessels of days gone by, our 37' ketch Nautilus perfectly combines traditional form and modern function.

With a large cockpit and wide cabin tops, you'll find plenty of comfortable seating options for all. Guests are free to move up to the bow for a great view while we're underway. The spacious cabin offers ample space for lounging, eating, or a brief respite from the elements. The galley has all the amenities of home, including an ice box and stove, and there is also a large head (bathroom) with push button facilities-- everything you need to create your ideal Portland excursion. Join us! We're certain you'll be glad you did.

Step aboard the sailboat Nautilus and experience the real magic of Casco Bay.

Relax and unwind as we silence the motor and let the wind take us sailing past lighthouses, between the islands, past historic forts, and even alongside playful porpoises and seals. With Captain Sam and first mate Crow as your seasoned guides, sit back and enjoy the view while you learn about our treasured Maine coast.

• What is the maximum passenger capacity? Nautilus's passenger capacity is 6 people maximum. This is determined by the U.S. Coast Guard so it is not flexible.
• Do infants count towards passenger capacity? Yes. The passenger limit is based on the number of human lives aboard, rather than by seating room.
• Do you take same-day bookings? YES we do! Our booking software with FareHarbor allows for same-day bookings. If a sail during a time slot you are interested in appears to be greyed out, you can give us a call to see if there are any seats remaining. One important thing to note: if the crew are not currently on the boat, it will take us roughly one hour to arrive at the boat and complete an all-systems safety check, so please call as far in advance as possible.
• Will we tip (heel) over? As a sailboat, the Nautilus is designed to lean to one side or the other with the pressure of the wind in her sails, with the extent of that heeling depending on the strength of the wind. If you’d like a more spirited sail, we recommend checking the forecast for winds of 13 knots (roughly 15 miles per hour) or higher. Morning and Sunset Sails tend to be the calmest, while Afternoon Sails are generally more lively. In Portland we usually receive the strongest winds in May, June, September, and October, while July and August are the calmest months.
• Is there a bathroom on board? Yes! We have a marine toilet, also called a head. The marina also has facilities for all guests in the form of 3 single-stall restrooms.
• Are life jackets required to be worn? Due to Federal law, anyone under 13 years of age is required to wear a life jacket on board any commercial vessel that is off the dock. Adults can choose to wear one if it would make them feel comfortable, but it is not required.
• What is your general cancellation policy? Please cancel one week in advance of your sail to receive a full refund. Cancellations made with under one week’s notice will not receive a refund unless they are due solely to sudden illness (see covid-19 policy below).
• What happens if it rains? Nautilus will still depart in mist, light rain, and passing showers. In the event of poor weather or unsafe conditions determined by the Captain at the time of the sail, we will offer to rebook your sail to a more pleasant day or provide you with a refund.
• Do you have a covid-19 / illness refund policy? If you become sick with covid-19, the flu, or any other contagious illness and need to cancel, you will receive a full refund. We appreciate your help in not spreading any illnesses to the crew!

Private Boat Tours and Island Adventures

Inquire about our tours.

Email Address

Interested In Interested In Family Adventures and Island Fort Excursions Maine Craft Beer Cruises Old Port Waterfront Tours Private Harbor and Lighthouse Tours

About Old Port Charters

Kids will enjoy exploring the island forts and geocaching treasure hunts on our interactive boating trips to multiple islands in Casco Bay. Adults can hop on board for a Maine craft beer cruise around the waterfront or our famous island bar hopping booze cruise.

Our Featured Charter Tours

Family Adventures and Island Fort Excursions

Maine Craft Beer Cruises

Private Harbor and Lighthouse Tours

Old Port Waterfront Tours

Private boat rides in the Old Port with fantastic up close views of Portland’s working waterfront.

Best Harbor Tours

Fun day exploring Fort Gorges.

Harbor Tours Portland Maine

A beautiful day for a lighthouse tour!

What Past Customers Say

Your Guide to the BEST Maine Sailing Tours | Windjammers, Sailboats, & Schooner Tours

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Everyone knows that Maine has a stunning coastline and breathtaking views of the Atlantic Ocean from pristine beaches to rugged cliff walks. But, have you ever considered seeing Maine from the water? Set sail on an exciting adventure on one of the best Maine sailing tours onboard a windjammer, sailboat, or schooner.

We think it’s the best way to view the Maine coast , and what could be more exhilarating than setting sail out of a Maine harbor aboard a tall-masted schooner? Down the coastline from the Downeast & Acadia region to the Southern Maine Coast , there are so many sailing excursions to choose from.

The best part? You can sit back and relax while someone else does the sailing and navigating. Or, you may lend a hand and hoist a sail if you prefer. There’s no better way to experience the beauty of Maine than on a historic sailing trip, so check out these options for your next visit to Maine.

Downeast & Acadia Sailing Tours

Downeast windjammer cruise lines.

If you’re looking for a variety of options for sailing, Downeast Windjammer Cruise Lines in Bar Harbor has you covered. Offering a Sunset Sail, a Morning Sail, and an Afternoon Sail, there’s a wonderful experience no matter the time of day. Each sail has its own vibe.

The Sunset Sail is the most popular cruise that Downeast offers. It includes live folk music, beer, and wine for sale. Or, enjoy sailing in Frenchman Bay during the Morning Sail, which is more relaxed but still offers breathtaking views of Acadia National Park .

The Afternoon Sail is perfect for those looking for a narration during the sail. The captain will point out points of interest, regale you with the local history, and discuss wildlife.

No matter the sail, you can bring a picnic of snacks along, and most sails are pet-friendly.

Downeast Sailing Adventures

Southwest Harbor

Step aboard the Real Maine for an unforgettable experience sailing around the Cranberry Islands, Acadia, and Somes Sound. This tour will take you by lighthouses, past gorgeous homes on the shore, and by working fishing boats.

Book a private charter or a group day sailing adventure for up to six passengers. Downeast Sailing Adventures has daily sails on its 33-foot boat Surprise and its 38-foot boat Swan .

Sail Acadia

Northeast Harbor & Southwest Harbor

Sail Acadia offers trips out of two harbors, Northeast Harbor and Southwest Harbor . Sailing trips can be either shared or privately chartered. Private charters can be catered to your preferences with sailing instructions or a stop at an island for a picnic included.

Book a morning sail for calm waters with gentle sea breezes and good opportunities to view local wildlife. The morning sail is suggested for first-timers and children.

Or, book an afternoon sail for stronger winds that will make the sailboat cruise faster. This sail typically sees seals along the route, and the captain will often give a narration of the wildlife and history of the area.

Another option is a sunset sail for a romantic experience. This sail will have you seeing gorgeous sunset views on calm waters.

Schooner Tours in MidCoast Maine

Schooner stephen taber.

If you’re looking for an all-inclusive overnight experience, book a sail aboard the 150-year-old Stephen Taber . Each sail includes accommodations in one of 12 cabins, meals, wine (on evening sails), a lobster bake and barbecue on the beach, and evening entertainment.

Guests can choose from a themed trip or a private charter from Rockland Maine . Themed trips are a lot of fun and span from three to six nights, depending on your preference.

Enjoy trips such as Culinary Explorations; ‘Wine, Dine, and Chocolate;’ Yacht Racing Regatta; Penobscot Bay’s Hidden Gems; and more. These trips are sure to be memorable experiences, and by the end of the trips, you’ll feel like family with the other guests on board.

Here are more MidCoast Maine boat tours that are part of the Maine Windjammer Association like the Schooner Stephen Taber : Schooner American Eagle | Captain Tyler King | Rockland, ME Windjammer Angelique | Captain Dennis Gallant & Candace Kuchinski | Camden ME Schooner Grace Bailey | Captain Sam Sikkema | Rockland, ME Schooner Heritage | Captains Sean Grims & Ben Welzenbach | Rockland, ME Schooner Ladona | Captain J.R. Braugh  | Rockland, ME Schooner Lewis R. French | Captain Becky Wright and Nathan Sigouin | Camden, ME Schooner Mary Day | Captain Barry King and Jen Martin | Camden, ME

A Morning in Maine

If you’re strapped for time and want a shorter sail, A Morning in Maine’s sailing trips are a wonderful experience. The two-hour sailing adventures take place aboard a 55-foot ketch that passes lighthouses and other schooners.

The morning trip is perfect for those looking for calm sailing. The mid-afternoon sail has windier conditions for a faster sail. Evening and sunset sails feature beautiful sunset views and a relaxing ride. Guests are often given the chance to try to steer the boat as well.

Schooner Surprise

The Schooner Surprise has been sailing for over 105 years, with 30 of those years setting sail out of Camden Maine . Guests can book a two-hour sail with views of the lighthouse, summer houses and views of Penobscot Bay .

These family-friendly sails let guests, including children, take the wheel while out at sea. Special sails include a Full Moon Sail that features live music during sunset and a trip lasting two hours into the night. Or, book a fireworks view sail or a Birding and Marine Life Tour with an ornithologist.

Portland & Casco Bay Sailing Tours

Portland schooner co..

Portland Schooner Co. sets sail from Portland Maine and cruises through Casco Bay for a delightful trip along the coastline and past lighthouses and ocean life, like seals. On the two-hour sail, bring your own picnic and even alcoholic beverages for a relaxing, scenic time on the water.

These sails are perfect for all ages. Sails take place throughout the day on one of the five historic wooden schooners. The sails are relaxing and do not include narration, but the crew is available to answer any questions that guests may have.

Maine Sailing Adventures

Maine Sailing Adventures offers traditional two-hour and themed sails through Casco Bay . What sets it apart from other sailing companies is its unique themed sails. Try an acoustic sail that features live music. Or, try a wine sail that includes a wine tasting for adults.

Have you ever heard of a yoga sail? This ship can accommodate up to 12 guests for a yoga class that you won’t experience anywhere else. Enjoy amazing views of the water while working on your poses.

Sail Portland Maine

If you’re looking for an intimate sailing adventure, Sail Portland Maine has you covered. Guests can choose a private charter or a public trip. The public trips’ capacity is 12 people, so you know that your sail won’t be too crowded.

Day and sunset trips are two hours in length and pass by all of the famous Casco Bay features — like historic forts, lighthouses, and if you’re lucky to spot them, seals. Guests are welcome to bring their own food and drinks, while bottled water is complimentary on board.

Schooner Tours on the Southern Maine Coast

The pineapple ketch.

Kennebunkport

There’s no better way to see the Kennebunk River than sailing on it. The Pineapple Ketch departs from Nonantum Resort for a dazzling trip along the river and the Kennebunkport coastline.

You’ll see gorgeous seasonal cottages, including the famous cottage of President George H.W. Bush. Enjoy views of the Goat Island Lighthouse, local harbors, seabirds, and seals.

Each sail includes complimentary bottled water and sodas, but guests are also welcome to bring their own food and beverages.

Silverlining Sailing

Silverlining Sailing offers one of the most intimate sails in Ogunquit Maine . Each boat has the capacity for up to six passengers, making for a small group sail. Sails typically last two hours, departing from the quaint Perkins Cove village.

There are five trips daily (weather permitting) from early morning through to a sunset sail in the evening. Enjoy stunning ocean views, gorgeous waterfront homes, views of local beaches, and harbors.

Since this is a smaller group sail, guests get the opportunity to try their hand at taking the wheel and steering the schooner.

Broad Reach Adventures

Broad Reach Adventures has two-hour sails, half-day and full-day sails, and chartered sails from Saco Maine , so there’s a sail to accommodate your busy schedule.

Each one allows guests to see beautiful views of the Saco River, Saco Bay, Biddeford Pool, Old Orchard Beach , and lighthouses along the way. Longer sails provide guests with the opportunity to disembark and explore uninhabited islands.

A unique feature that Broad Reach Adventures offers is the opportunity to add a massage or professional photographer. These experiences are available on certain dates and times, so book ahead if you’re interested in these add-ons.

Sailing Lessons & Boat Rentals

If you want to learn to sail, sailing instruction is often available as part of your charter package.  Private charters  of sailboats on the Maine coast allow experienced sailors to explore the coastline on their own.

Private sailors will find  hotel marinas  for lodging in Maine’s best harbors. If you time your sailing cruise right, you might witness seals, porpoises, whales, or other tall ships.

Watching the sunrise from the deck of a schooner is one of life’s simplest, most satisfying pleasures. Of course, the spectacular Maine scenery is always included on your sail.

Set Sail on Sailboat & Schooner Tours From Maine This Season

Now that you know about all of the sailing trip options, it’s time to set sail into the open waters of Maine. From two-hour trips of the bays and harbors to overnight excursions, there’s an experience awaiting you on your next getaway.

Each Maine sailing company offers its own unique trips aboard safe, well-maintained schooners. Relax, unwind, and feel the ocean breeze in your hair as you cruise through the lapping waves of Maine’s Atlantic shoreline.

The VisitMaine.Net team is the small team of authors and editors that research and write our in-depth guides throughout the site and update past articles to make sure they're still super valuable to you. We have one goal: to help you fall more in love with the state of Maine!

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Travel+Discover Maine – The unofficial guide to exploring the great state of Maine. Not affiliated with any official tourism entities.

Copyright Travel+Discover Maine 2024 Images Courtesy Greg and Heather Burke unless otherwise noted.

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SEAGLASS SAILING CO.

We're Not Just Better, We're the Best

S/V Seaglass, a 1965 Pearson Rhodes 41 turns heads everywhere she sails.  

The 41' masthead sloop can comfortably accommodate up to 6 passengers for 1/2 day, full day, and overnight voyages around Casco Bay.  

A comfortable cabin and spacious cockpit provide gracious space for relaxing and entertaining.  

Captain Paul Leddy, who grew up sailing the waters of Casco Bay, is looking forward to helping you plan an unforgettable Maine Experience.  

Contact us today, or learn more about voyages aboard S/V Seaglass .  

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Captain Paul and Seaglass Sailing Co. are here to share the beauty of Casco Bay and a passion for sailing with all of their visitors. Questions, comments or special requests? We’d love to hear from you, so don’t hesitate to reach out today.

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Copy My Trip: 3 days in Portland, Maine

Sep 12, 2024 • 6 min read

Be inspired to spend a weekend in Portland, Maine, with these top tips from a recent visitor. Rachel Lewis/Lonely Planet

Lonely Planet’s senior social media manager, Rachel Lewis, recently returned from a weekend with her wife in  Portland , Maine . Here she shares her trip highlights and what to prepare for before you go.

I’ve always had a clear picture in my head of what visiting Portland, Maine would be like, and, honestly, it was pretty stereotypical: buttery lobster, stripes and linen, setting sail from the Old Port and thumbing through pottery at local shops. I’d never been to Maine, period, but when I told my grandmother (who’s from Massachusetts) that I was planning a long-weekend trip with my wife, she had two recommendations: eat as much as you can manage, and go to the locally owned Cool As A Moose (and buy her a mug for Christmas – on it, Gramma). My wife and I landed with empty tums and space in our luggage for goodies, and hit it. 

I want to help you do the same. Here are a few things that made my weekend in Portland so memorable.

Where did you stay? What was the vibe?

The Longfellow Hotel in the West End is a newly opened boutique hotel with a heart for sustainability. On our first morning in Portland, we tested out room service with a breakfast order of an iced oat milk latte. I got just what I was craving, and my wife couldn’t stop raving over her breakfast sandwich – baked egg, spicy mayo and pepper jack on an English muffin.

I was particularly impressed with the creative mocktail menu at its dinner and drinks venue, Five of Clubs . Finding good alcohol-free drinks when traveling sober (or sober curious, in my case) can be tricky, but the “functional cocktails” are stunning. I had a Rosarium – bitter orange, earl grey, pomegranate – and a Vacationland Refresher – wild Maine blueberry, cardamom, lemon soda. The earl grey was a great intro to the -ber months. 

The spa, Astraea , has an  infrared sauna  (reserve it in advance!), and you can get your very own space with a bathroom, rain shower and sauna. There are a few different massage options. We chose Mindful Dreams , a meditative, rhythmic full body massage ($145/person for 60 minutes). Sip peppermint tea and feel wonderful as you lounge about in your new skin (okay, I know that’s not how it works, but it’s how it feels).

What was the best thing you ate or drank?

I'm not even going to attempt to single out a "best" meal in Portland, but with its foodie reputation , you can expect to dine well. These are the dishes, snacks and flavors that stood out for us.

Brickyard Hollow Brewing Company  is a local chain that makes gourmet pizza from Freeport to Yarmouth (the original) and beyond. We went with cheese pizza, and it was beautiful in its simplicity: 12 inches of cheesy goodness with an olive oil base. Next time, though, I’d grab something more experimental, like its blueberry pizza with Maine blueberries, rosemary ricotta, roasted shallots and lemon zest.

Green Elephant , a vegetarian bistro, does not take reservations, so get there at 11:30am when it opens for lunch. Grab yourself some deep-fried vegetarian spring rolls and king oyster mushroom tempura. If you’re a vegetarian like me, you’ll appreciate a space where you can eat literally anything without having to triple-check that the allegedly vegetarian pseudo-meat you’re taking a bite of is 100% not meat. Go for the ginger noodles and appreciate the spice (make it vegan by skipping the egg).

Another tasty lunch option includes Benkay, a Japanese restaurant and sushi bar. Consider the teriyaki tofu; it’s fast, hot and surrounded by colorful veggies. For a filling dinner, we hit  Black Cow , a burger joint. I got a veggie burger with a mushroom lentil patty, iceberg, pickled red onion, radish and black garlic mayonnaise on its signature black cow bun.

When you need a break during your Portland wanders, grab a donut at Holy Donut (consider the blueberry glaze).  Navis Café on Thames Street – about a block from the water – serves great egg-white bagels and iced decaf vanilla lattes for breakfast on the move.

What was the most touristy thing you did?

We wrapped up our final day by hopping on a sunset cruise. Portland has quite a few options, but no matter what you pick, book in advance. We saw many excited tourists get turned away when they tried to buy tickets just before sailing. We chose the Casco Bay Sunset and Lighthouse Cruise ($52/person) to see Diamond Pass and the Calendar Islands and were glad we arrived early – we snagged stellar seats on the upper deck. 

Where is the best place to shop?

In Maine’s historic Arts District, swing by Soleil , a gift shop where you’ll want pretty much everything, especially if you’re the sort of traveler who wishes they had a cuter key chain (how about a  dog wearing a sweate r?), an adorable lobster toiletry bag or a notebook with a metallic croissant on the cover.

Cross the street and make your way to Loquat . It’s alive with design, literally, considering that you can see artists working in the back. Stock up on shea butter or grab a Shirt of the Week . If all this color makes your artsy heart grow three sizes, consider swinging by any of the galleries along the way or nearby. The Portland Museum of Art is the obvious choice, and it’s free on Fridays (otherwise it’s $20 per adult). You’re almost certainly going to run into spaces showcasing student work from the Maine College of Art & Design, so keep your eyes peeled as you stroll.

What essential items did you pack?

The name of the game is layers and comfy, grippy sneakers for lots of strolls on cobblestone streets and stepping onto a sailboat. Portland is pretty chill. We saw loads of people in sneakers and jeans, and quite a few people in all black. I packed a pair of jeans that could be dressed up or down, a light sweater and a linen chore jacket for layering, and a baseball cap in case of rain. Accessories are handy for nicer restaurants where you want to feel like you dressed up without dressing up.

What other tips do you have for someone planning a similar trip?

• When to arrive: Give yourself at least three days – we arrived Friday evening and left late Monday afternoon, and were glad we had time to laze about in between activities. 
• How to get from the airport: For ease, fly into the Portland International Jetport, just 2 miles from downtown Portland. From there, hop in a rideshare. Our Uber was $12 and took less than 20 minutes. Or, if you live within a few hours of Portland, consider taking the train; prices are reasonable, and bonus: you can get in views of foliage if you come during fall.
• Getting around town: Portland is walkable as long as you choose accomodations near the hub where you want to explore. We zeroed in on the West End and Old Port.

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Sail Portland Maine started in 2019 as the result of Captain Ian Glass’ lifelong love for sailing and desire to make dreams a reality. From a young age, Captain Ian was always interested in the water. His passion stems from a long line of sailors in the family and to which Ian has created his own path in the maritime world. At 19 years old, Ian left Florida and went to crew on a schooner in Camden, Maine. After three days of sailing around Penobscot Bay he was hooked, and as they say – the rest is history. Now he spends his days captaining unique, intimate charters in Casco Bay for all to enjoy!

Ian has experience crewing and captaining many different types of vessels. From private sailing yachts to commercial supply boats and his favorite, the traditionally rigged gaff schooner. His journeys saw him cooking on-board yachts for royal families and crossing all of the world’s major oceans. He will be glad to share his personal story aboard one of his two boats , explain the history of Portland, and share interesting maritime history as you cruise.

Portland, Maine Charters in Casco Bay

The best part about booking a trip with Captain Ian is that he can create custom charters in Casco Bay for you! Whether you want to cruise to one of the local islands for a dinner out, host an elopement or micro-wedding , or simply enjoy a trip with loved ones, let us take you there! Our goal is to give you the trip of a lifetime and provide the best charters in Casco Bay.

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Shore Excursion Details

The white mountains by conway scenic railroad & bus, portland, maine.

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• 7 1/2 hrs Estimate Duration

Travel through the scenic White Mountains in a meticulously restored 1950s-era railway car that evokes a period when life was more leisurely. You will get a hint of the natural beauty that lies ahead on the 1.5-hour scenic bus drive to North Conway, a delightful town in New Hampshire near the White Mountain National Park. After a bit of free time to explore, you will board the Conway Scenic Railroad in the 19th-century train station and settle in for a breathtaking ride through the majestic White Mountains, which cover nearly a quarter of the state. Along the way, you will pass over towering trestles, through Mount Washington Valley and up into an alpine setting that is spectacularly photogenic. Enlightening commentary will enhance the experience by describing the points of interest in fascinating detail. You will eventually disembark at the late 19th-century Crawford Notch train station for the two-hour return drive to Portland.

• Ride the vintage Conway Scenic Railroad into the majestic White Mountains. • Enjoy panoramic views of the White Mountains and its namesake national park. • Pass over train trestles, through Mount Washington Valley and into an alpine setting. • Enjoy the train’s historical ambiance and a boxed lunch along the way.

HELPFUL HINTS

• Dress in weather-appropriate clothing. • Wear flat comfortable walking shoes.

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Scenic & City Tours

Activity level:.

• 3 Challenging