sailboat charters rock hall md

Sailing the Beautiful Chesapeake Bay from Rock Hall, MD

Sailing charters.

Sunset sail, it's just a phone call away.

(302)545-8149

Day, Sunset, and overnight charters

s/v Sol Searcher

is a 2011 Beneteau Oceanis 50 .  She is well equipped and quite comfortable for sailing charters.  The cockpit has ample seating for 6 guests and a head (bathroom) is available for your use.  Dodger and bimini provide protection from the elements but the foredeck is always open to sunset sail lovers.  A full enclosure provides the ultimate protection in the shoulder seasons.  She is a CE CLASS A (designed for large sea voyages everywhere) yacht and carries all USCG safety requirements.

Captain Joe

"I love floating on the water, there's something about it that completes me."  joe, USCG Master 50GRT, Auxillary Sail, Assistance Towing

I have been sailing all of my life.  My father built his first boat, a little skiff with an outboard motor.  He eventually became interested in sailing and purchased a GP14.  He and friends would sail much of the upper Chesapeake Bay in that little boat.  One of the infamous stories is negotiating to pay only half the ramp launching fee at Sandy Point State Park and heading north to Elkneck State Park.  Quite an ambitious undertaking for three guys in a 14 foot sailboat.  By the time I came along our family had a Meridian 25 docked in Havre de Grace, MD.  By the time I turned seven my parents had upgraded to a Sabre 28 named "Poinciana," after the song, and I would sail on that boat for the next 22 years before losing my dad to cancer.  Over those years I got to share time on the water with him in various boats of my own, including a Hobie 16, Precision 23, and a Grady White. In 2005 I bought my dream boat, a 1990 Sabre 38mkII named "Voila", he truly would have appreciated that boat.  She was the boat that Sabre took to the NY boatshow that year, he would have been on board her then.  My mom did sail many miles on "Voila."  Now I have Beneteau Oceanis 50 for my sailing charter . She's big, beautiful, fast, and has all the comforts of home. Come experience a Chesapeake Bay sunset sail .

All sails 6 person maximum

3 Hour $99/person Mon-Thur at 10a

Private sails 6 person maximum

3 Hour $450 (each additional hour  $150)

7 Hour $950

Weekday Overnights

1 Night $2,100

2 Nights $2,900

3 Nights $3,600

4 Nights $4,200

Fri, Sat, Sun $3,350

longer sailing charters... call for pricing

It's really simple!

I'll be ready to go and the boat will be ready to go on time.  You can bring food and drinks.  If the weather is going to bad we can reschedule.  Just pick a date and drop me a line. Sunset sails leave the dock 2.5 hours before sunset.

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Frequently asked questions.

Please reach us at [email protected]  if you cannot find an answer to your question.

Absolutely NOT!  I can handle the boat by myself, I may ask you to help with lines while docking or if you want to drive or trim the sails you can.  If you just want to decompress and watch the world go by that's fine too. 

In a word, no.  However, this is not a handicap accessible activity.  If you can walk  a hundred yards and do steps you will be fine.  For the very young, kids love the boat.  They'll want to run all over, push buttons and generally drive their parents nuts.  I'm fine with kids, have a couple of my own, I just ask you look after yours. 

Six is the maximum number of guests I can take sailing.  This does not include the captain or crew.  

Yes, you are more than welcome to pack a cooler with food and drinks for your day on the water.  I would recommend that you keep it simple, It may be easy to eat a sandwich while sailing but it is no small task to make one.  

Don’t forget your cameras!  Sun screen ( please, no sprays , it stains the boat), hats, and sunglasses usually come in handy and there is always the possibility to get wet, a light rain jacket made be prudent.  Non-marking shoes are required or you can go barefoot.  The spring/fall days start cool but tend to warm up in the afternoon and then cool down at sunset, so dress in layers.

The bay is not like the open ocean, not many people have gotten seasick on my boat.  If anyone in your party needs to take  motion sickness meds , please tell them to follow the instructions on the label, which will most likely tell them to take it hours ahead of time.  

Rock Hall is a quaint little town on Maryland's eastern shore.  Once known for waterman it is now primarily a tourist destination.  There are numerous restaurants and lodging options and the town has many festivals throughout the year.  More information can be found on www.rockhall.md.com

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If you find yourself in Rock Hall looking for a boat charters and are thinking of a sunset sail just give me a call.

Experience Sail LLC

20786 Rock Hall Avenue, Rock Hall, Maryland 21661, United States

(302)545-8149 / [email protected]

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Fully Crewed Sailing Cruises Aboard 41' Sailboat in Rock Hall, MD

Enjoy a fun day on the bay relaxing and taking in the scenery of Rock Hall, Maryland! Book the Fully Crewed Hunter 410 Sailing Yacht for up to 4 person. Rates as low as $150 per hour and a minimum booking of 4 hours. Rates: • Full day (8 hours): $1000 • Half day (4 hours): $600 • 2 days/1 night (8am day 1 to 2pm day 2): $2000 • 3 days/2 nights (8am day 1 to 2pm day 3): $2400 What To Expect Onboard: S/V Bay Poet is a 41-sloop. She is fully furnished including a full galley, Bluetooth stereo, and large airy heads.  We can accommodate up to 4 guests for multi-day cruises or up to 6 guests for day cruises.  The aft cabin is large and spacious for 2 people.  Additional guests will be berthed in the main salon.  We provide all bedding and linens for multi-day trips. Bay Poet is documented for coastwise trade for a six-pack charter.  Our sailing season is May through October. Captain Rob is a fully licensed merchant mariner with experience on recreational yachts up to 60-feet.  He has worked aboard the 530-ton Chesapeake Lightship. More recently he has been a Relief Captain aboard the New Jersey State Tallship, the Schooner A.J. Meerwald. Captain Rob also holds license endorsements for auxiliary sail and commercial assistance towing.    First mate and chef Theresa has planned and prepared meals aboard sloops and catamarans from the French West Indies to the Aegean Sea. She embraces local ingredients and prepares rich, satisfying meals from them. Theresa is an accomplished sailor in her own right. She is skillful at the wheel and frequently takes the helm for docking and anchoring. She is a gracious hostess who can never do enough for her guests.  S/V Bay Poet is available from May 1 through October 31. Daysails are available any day with Capt. Rob and fully crewed sails are possible Friday afternoon through midafternoon Sunday.  Scheduling multi-day cruises is more flexible.  All bookings must be confirmed at least 3 days in advance. S/V Bay Poet is equipped with commercial-grade personal floatation devices (PFD) for people who weigh at least 90 lbs.  If you are bringing children who weigh less than that or who are of a generally smaller build, the client guardian will be responsible for providing a correctly fitted PFD for each such child.  The child must wear the PFD anytime they are on deck whenever the vessel is underway.  They are not required to wear it while the vessel is at anchor or secured in a marina.  They also do not need to wear it when below deck.  The Captain will inspect the PFD upon boarding to verify that it is legal for its intended use.  Please check with us in advance if you need guidance in selecting an appropriate PFD for a child. Guests are welcome to assist the crew in sailing the vessel if they so desire.  However, guests are not required to participate in any way in operating the vessel, except that they must follow the instructions of the crew at all times especially during emergencies.  They will be given a briefing on various routine and emergency situations before departure.  Clients will also be given instructions on using the various systems onboard such as lights, water, and sanitation systems.  Guests are encouraged to ask questions at ANY time. If you have any questions, we can answer those through GetMyBoat’s messaging platform before you pay. Just hit, “Request to Book” and send us an inquiry for a custom offer.

Starting from

• ₽13,723/hr 4 hrs min

Check Availability

Listing accuracy, departure & return, vessel & equipment, communication, itinerary & experience.

Captain Rob made the trip memorable with the beautiful views of the Chesapeake sunset and anecdotes of the area and his marine career.

Rob has worked as an engineer in the telecommunications and defense industries.  He retired from Miku, Inc. as the Director of Software. Rob has a BS in Electrical Engineering and an MS in Solid State Physics. Rob has been in love with sailing since the mid 70's.  He has been sailing every year since 1989.  As a member of the Sailing Club, he held several posts including Commodore and Training Coordinator.  Rob loves the Chesapeake Bay and will share that love with all who will listen.  Other experiences include two Lucent Regattas in the Netherlands and as captain of a 45-foot tugboat as a teenager. Rob holds a 200-Ton Master's license with Auxiliary Sail and Assistance Towing endorsements.  He has organized flotilla cruises all over the Chesapeake Bay, Europe, and Caribbean.  He was recently added as a Charter Captain by Dream Yacht Charters.  He worked two seasons as a Relief Captain aboard the state tallship of New Jersey.

Features & Details

• Galley Stove & Oven
• Life jackets/required safety gear
• Single Engine
• Wheel steering

Approximate Location

You’ll get directions to the departure location when you make a booking.

Cancellation Policy

Full refund up to 10 days prior.

Additional Terms & Information

Trip Pricing Two- and three-day weekend trips have fixed base prices regardless of the number of guests.  S/V Bay Poet and her crew can accommodate a maximum of 4 guests.  The overall trip price may be higher if the guests wish to spend one or more nights at a marina that is not the home marina for Bay Poet.  Also, special requests regarding menu selection, group activities, day visitors, or any other extra services may add to the total trip price.  We will provide an updated trip price quote to the primary client before accepting any reservation.  The quote will take into account information provided by and requests made by the Primary Client. If special requests are made after receiving a price quote or after a payment has been paid, we reserve the right to either adjust the price of the trip in order to incorporate the updated requests or decline the special requests if the updated price is not acceptable to the client.  Any additional costs to be paid as a result of the special request will be due in full at the time of the final payment.  Special requests made after the final payment may be declined.  However, if such a request is accepted, any additional costs to implement the request must be paid at the time the request is accepted. Cancellation The Primary Client may cancel the trip up to 10 days before departure and receive a full refund of the deposit.  If the final payment is not made 10 days before departure, we reserve the right to cancel the trip in its entirety.  The payment will be refunded less any non-refundable expenses which may have been incurred (i.e., non-refundable marina fees, special purchase items, or things which cannot be returned, etc.).  If a client cancels a trip less than 10 days before boarding the vessel, all monies paid will be refunded less any non-refundable expenses which may have been incurred (i.e., non-refundable marina fees, special purchase items, or things which cannot be returned, etc.) and a $100 cancellation fee. If we have to cancel a trip for reasons not related to safety or Coast Guard restrictions, all monies paid will be refunded to the Primary Client. Trips will sail regardless of weather conditions unless in the opinion of the Captain and crew, forecasted weather conditions present an unacceptable risk to the vessel and those aboard.  Furthermore, if the Captain of the Port of Baltimore restricts navigation on any or all of the waters for which a trip is planned, a given trip may not be able to proceed as originally planned.   In either case, the Primary Client may choose to reschedule the trip or to receive a refund less the cost of any special or custom items purchased.  Those items will be conveyed to the Primary Client as appropriate.  If the Captain of the Port restricts navigation on any or all of the waters for which a trip is planned, a given trip may be able to proceed but not as originally planned.  Unless a critical destination is made unavailable, we will deem the trip as viable and plan to sail accordingly.  If a critical destination is unavailable as a result of action taken by COTP, the Primary Client may choose to re-plan the trip for the same dates, to reschedule the trip, or to receive a refund less the cost of any special or custom items purchased Notification of cancellation by either party may be made by email.  The party receiving notification of cancellation must explicitly acknowledge the notification by any means.  If the receiving party does not acknowledge the cancellation within 48 hours of its being sent or more than 24 hours before boarding the vessel, whichever is earlier, the sending party must call the other party.  Leaving a voice mail message shall be deemed adequate at any time. Guidelines and Requirements for clients The Primary Client is the point of contact between us and all guests who will participate in a given trip.  To avoid confusion and errant messages, we will not entertain contact with anyone other than the Primary Client.  We will provide information to the Primary Client that should be distributed among all guests.  This includes information on what to expect, what to bring, and what not to bring.  Firearms, pyrotechnics, drones, and controlled substances may not be brought aboard or used aboard Bay Poet at any time.  This list should not be considered as all inclusive.  Smoking (tobacco only) is permitted onboard and then only in the rear of the cockpit.  Pipe and cigar smoking is never allowed.  Smokers must monitor and police their own ashes and butts.  The entire party will be held responsible for any damage caused by careless smoking. Use of illegal drugs or otherwise controlled substances is NEVER permitted and will lead to the IMMEDIATE termination of the charter. We welcomes families of up to 4 people.  The minimum age of any children in your party is 12.  There must be at least one adult for each child under the age of 14.

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Haven Harbour Marina

Deepwater Slips

Floating piers, explore virtually.

Gasoline $4.65 ; 4.30 ; 3.94 (8/9/24)

Diesel $3.68 ; 3.40 ; 3.11   (8/9/24)

Prices displayed are per gallon retail, 50+ gallon and 100+ gallon quantities, respectively. Rates include tax and are subject to change.

Resort and Service Amenities

Head, laundry and bathhouse facilities are available on-site in addition to an air-conditioned slipholder and guest lounge, fitness center, picnic pavilion and two swimming pools. Surf the internet with ease on complimentary high-speed Wi-Fi.

Dining and Lodging

Enjoy a delicious meal or drink at our seasonal waterfront Passages Bar & Grill.

Book a stay in our 19-room shore-side Inn, offering guests stunning views of Swan Creek with a variety of flexible stay options, pet-friendly suites, full-house lodging and complimentary continental breakfast served fresh daily by our resident inn manager.

Docks and Grounds

Meticulously manicured floating and fixed piers meet gorgeous grounds of lush gardens, a children's play area and beach, bicycles, kayaks, paddleboards, outdoor games, barbecue grills, dog walk and more.

Haven Harbour Marina also features a dinghy dock. To use while dining or enjoying cocktails at Passages Bar & Grill, please hail our dock staff on VHF-16 prior to your arrival. We will accommodate dinghies for up to two hours while dining. Docking dinghies for longer than two hours requires a day pass, which may be purchased in advance or while on-site.

Charters and Cruises

Charter a sailboat out of Haven Harbour Marina through Haven Charters and experience the Chesapeake Bay like never before.

Book a cruise aboard a 12-person tiki barge, piloted by owners Jacki and Dave of Haven Charters and docked at Haven Harbour Marina's Reception Center. Learn more at RHTiki.com .

Haven Harbour Marina facilities, grounds and docks are monitored 24/7 for added security.

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Speak to our helpful guest representatives in the Marine Store for more information on local transportation solutions.

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Our yacht service facilities rank among the best in the region. On-site equipment and accommodations include a 50 MT travel lift, crane, hydraulic trailer drop-in and haul-out service and in-water towing.

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Our highly experienced ABYC- and ABBRA-certified in-house boatyard technicians ensures a quality and professional service experience. An on-call service technician is also available every weekend. 

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Dry, wet, winter, locker, dinghy and sail storage is available on-site year-round.

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Maryland’s Sailing Season Nears | the 3 Best Rock Hall Charters

As much of the country battles the latest polar vortex brought on by a blast of Arctic air, it’s easy to daydream about summer’s inevitable arrival. Maryland’s sprawling, peaceful Chesapeake Bay is, of course, best known for its many marinas and sailing communities. Thus, the Osprey Point team would like to shine a light on three Maryland sailing charters, all of which are located right here in Rock Hall, the “Pearl of the Chesapeake.”

An Unforgettable East Maryland Sailing Voyage

Before we know it, spring will give way to summer’s golden hearth, providing nothing but clear, sunny skies and idyllic temperatures set in the upper 70s and low 80s. The Chesapeake Bay itself spans nearly 4,500 square miles, allowing an innumerable number of sailboats to survey its aquatic terrain. Thankfully, Osprey Point Marina is home to one of Maryland’s finest sailing charters, Shardana. In fact, Osprey Point is within walking distance of two of the state’s most beloved charters. The time to book an excursion is now before availability washes away. But first, please read more about Rock Hall’s top three sailing experiences.

1. Shardana Sailing Charters

Osprey Point Marina’s very own Shardana Sailing Charters remains one of the region’s most intimate excursions. These “luxury-based” adventures offer something that most East Maryland sailing charters simply cannot: sheer privacy. Shardana, a custom-built, 42-foot sailboat, ushers families and small groups out to sea en route to Chesapeake Bay’s quietest, most picturesque locales. Choose between a half-day, full-day, or sunset charter. Because Shardana encourages a “BYOB” atmosphere, sailors can bring along a bottle of fine wine, a growler of craft beer, or a small cooler filled with hard seltzers. And, once the journey is over, you’ll only be steps from your historic accommodation .

2. Blue Crab Chesapeake Charters

Blue Crab is located on the other side of town inside Rock Hall Landing, home to Waterman’s Crab House. While Blue Crab does offer a wide variety of cruises, most curious travelers cannot resist the 90-minute, $35 trip. Twenty-plus years in the making, the Blue Crab team has perfected its touristy appeal. “Island Girl,” a 43-foot center cockpit sailboat, hosts everything from weddings to classic sunset sails and the “ cruise-n-crabcake .”

3. Haven Charters

Neighboring Haven Harbour Marina is home to Haven Charters, Maryland’s premier self-guided sailing voyage. Because Haven is a bareboat operation, you’ll need recent sailing and navigational experience, as well as references. What makes Haven Charters even more unique is that they boast approximately 25 vessels, ranging from $1,475 to $2,900 for a two-day weekend trip. Most folks survey the Chesapeake Bay by day and return to Osprey Point in the evening hours for dinner and a good night’s sleep.

Looking for a kid-friendly alternative? Try a public sail via Chestertown’s Sultana Education Foundation .

Historic Accommodations in Rock Hall, MD: Osprey Point

To book a long-overdue summertime sailing escape to sunny Maryland’s cutest small town, please check availability online .

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Chesapeake Bay Sailing Cruises Sharp St. Pier -  Rock Hall, Md 410-708-1803 - [email protected]   90 Minutes - Up to SIX Guests $35 per person Serving Rock Hall for 25 Years!   Trip Advisor #1 "Thing to do" in Rock Hall Day Sails - Sunset Cruises - Privates - Weddings - Special Occasions - Lessons and Instruction 

Rock Hall faces west, looking out upon the open Chesapeake Bay.  Its privileged location permits one to witness some of the most dramatic and sensational sunsets imaginable anywhere on the east coast.  When the sunset fades, and darkness comes, the harbor lights reflect out upon the water, stretching for awhile across the rock jetty harbor entrance where they disappear into a horizon lit only by the distant sky of Baltimore.

Rock Hall's Original Sunset Cruise

  Still just $35.00 per person ( 4 person minimum)  90 Minute Cruises Completely private cruise or groups of 5-6 passengers $210.00