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Martha’s Vineyard Private Sailing onboard 42ft Pearson Sailboat

Martha’s Vineyard Private Sailing onboard 42ft Pearson Sailboat

Name: Martha’s Vineyard Private Sailing onboard 42ft Pearson Sailboat
Brand: Pearson
Price: 250 USD
Availability: OnlineOnly
Rating: 5.00 (9 reviews)

With Captain

5.0(9 reviews) ·

11 bookings

the United States,Massachusetts,Tisbury,Sailing

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This date is available.

⛵️ Private Sailing Charters Around Martha's Vineyard $250/hour | 3-hour minimum | Up to 6 guests Step aboard Our Passion, a comfortable and well-equipped 42-foot sailing yacht, and enjoy a completely private and customizable charter in the waters around Vineyard Haven, Oak Bluffs and Edgartown on Martha’s Vineyard as well as Cuttyhunk Island. We’re a husband-and-wife captain team with over 40 years of combined experience, offering relaxing, memorable, and safe sailing adventures for couples, families, and small groups. ⭐️ What’s Included: - Your own private sailboat (Pearson 422) with licensed captain and crew - Flexible departure points: Edgartown, Vineyard Haven, Oak Bluffs, New Bedford, Mattapoisett, or Dartmouth - Spacious shaded cockpit + open seating at bow and stern - Swim platform & ladder — perfect for jumping in or dipping your feet - Hard-bottom dinghy for beach visits or exploring islands - Personalized itinerary based on your goals: relax, explore, learn, or celebrate - Optional sailing lessons or hands-on experience at the helm 🗺 Popular Charters: - Day sails around Vineyard Sound or Buzzards Bay - Sunset sails and full moon cruises - Cuttyhunk day or overnight trips - Island hopping between the Vineyard and mainland - Beach landings at private coves for sunbathing or swimming 👩‍✈️ Your Crew: We are both USCG-licensed 50-ton Masters, certified in first aid, open-water rescue, and advanced survival at sea. Safety and hospitality are our top priorities—and we love sharing our passion for sailing. 💬 What Guests Say: "We had the best day of our trip aboard Our Passion. The boat is stunning, the captains are true professionals, and the experience was completely tailored to what we wanted!" 📞 Ready to Book? We’re happy to answer any questions and help you build your perfect day on the water. Send us a booking request or message now to secure your preferred date.

Mason

14 total bookings

Superowner

Capacity: 6 guests

Sailing: Cruising Monohull

Reviews

5.0 (9 reviews)

Listing Accuracy
Awesome
Departure & Return
Awesome
Vessel & Equipment
Awesome
Communication
Awesome
Value
Awesome
Itinerary & Experience
Awesome

36 photos have been added by reviewers who booked this listing.

MS
Melvin

Capt. Mason and Capt. Lynne are ABSOLUTELY AWESOME. Their 42' sail boat was incredible and my party of 5 had a fantastic time on our charter. They are knowledgable, accommodating and true sailors through and through. My wife and I HIGHLY recommend Capt. Mason for any charter needs you may have, using his yacht or any other!
SS
Stephanie

Mason and Lynne were amazing captains on a private sail charter! So easy to communicate with throughout my planning process and amazing people overall! Had a great time being on the boat with them! Would absolutely recommend them and this experience!
JS
Jonathan

An afternoon on the water aboard the Our Passion is like an afternoon in paradise. The sailboat is gorgeous and comfortable, the skipper and crew more like instant old friends, and there’s no better place to sail than Martha’s Vineyard. An 11 out of 10 experience.
Rodney

Highly recommend if you’re looking for something different to do than what all the other tourists are doing when visiting Martha’s Vineyard, you might want to consider contacting Mason for a peaceful & relaxing sailboat ride to see the beautiful coastline of MV that most don’t get to experience while on land. We’ll definitely be back next year to do another trip
GE
Gerald

By far the best part of our trip to Martha’s Vineyard and the highlight of my girlfriend’s birthday was our time on Captain Mason and Captain Lynne’s boat. They thought of every detail, including birthday decorations and helping me with multiple surprises, took us to the most beautiful spots along the coast and harbor, and even let us partake in a super unique light show boat parade experience. This is by far the best value for money and most unique and relaxing / beautiful experience you could have in the Vineyard. Please trust me and book! Mason and Lynne are also wonderful people who really try to make your experience as amazing as possible. Thank you so much for everything!!!

Mason

14 total bookings

Superowner

I have a USCG 50 Ton Master Near Coastal w/ Sailing and Assistance Towing endorsement and over 1500 sea days. I take safety of the vessel and our guests first and foremost. I am a Red Cross Lifeguard and keep my CPR/First Aid certifications active. I am member of random drug testing pool and do not consume alcohol. I only hire drug tested and fully licensed crew members.

Features & Details

Pearson
42
Capacity: 6 people max

Safety Equipment

Life Jackets (1)

Operating Equipment

Autopilot

Dinghy/Tender

GPS ChartPlotter

Inverter

Depth Sounder

Guest Amenities

BBQ

Cabins (1)

Oven

Sun Protection

Toilets (1)

Leisure & Entertainment Equipment

Bluetooth

Departure Location

The boat's approximate location on a map

You’ll get helpful information for your departure after your booking is confirmed.

Street Address For Arrival

19 Owen Park Way

Tisbury, Massachusetts, 02568

United States

Departure Location

Same as Street Address

Cancellation Policy

Free cancellation up to 5 days before your trip.

Additional Terms & Information

If we cancel for weather there is a full refund. If you cancel for weather but it is still safe to make the trip, as determined by the captain, you pay the full amount of your rental booking. We reserve the right to consider the charter as having started on time if you are more than 15 minutes late. The scheduled time that the charter was supposed to end will remain the end of the charter and you will be charged for the full amount of time originally booked. Damages or cleaning fees will be charged to the charterer if the vessel is damaged due to the passengers own actions. Passenger will be expected to sign a liability waiver before the charter begins. No excessive alcohol drinking aboard. No smoking tobacco on board. Any drug use or possession, including marijuana, medical or recreational, will immediately end the charter and the captain reserves the right to discharge all guests on land at the nearest safe harbor.