Sailing in Martha's Vineyard
3 boats available
The best out of 3 deals in Martha's Vineyard - enter dates to check availability
Top Sailing in Martha's Vineyard
Island Sailing Tours
Martha's Vineyard3 Hour – Sailing CharterEnjoy a 3-hour sailing adventure aboard Tandemeer, our 60-foot luxury Ketch, exploring Vineyard Haven Harbor, Nantucket Sound, and Vineyard Sound. Feel the wind in your hair, take in stunning views, and dive in for a swim whenever you like. Charters can start at any time between 10 AM and 4 PM—just give us a call to schedule your preferred departure.Price for up to 6 peopleUS $750- 4 Hour – Sail Around The BayThis is a four-hour sail around the bay. This will allow ample time for a mix of sailing, swimming, exploring, and byob/food dining. We can cater to your desires and make a custom itinerary that works for you and your guests.Instant ConfirmationPrice for up to 6 peopleUS $1,250
- 2 Hr – Harbor & Bay Sailing TourEnjoy the world-class sailing grounds of Buzzards Bay and the picturesque coastlines of Dartmouth, New Bedford, and Fairhaven, Massachusetts. Whether you want to hoist the sails and take a turn at the wheel, or simply sit back, relax, and enjoy the harmony of sail and sea, an excursion on Omoo will be the highlight of your day.Price for up to 6 peopleUS $440
What boaters said about Sailing
- 5.0/5(4 Hour – Sail Around The Bay)
Fun time with great people
Captains Lynne and Mason were very engaging and willing to expertly answer all of our questions about sailing. thisnis a great experience!
- 5.0/5(3 Hour – Sunset Sail)
Amazing experience!
My teen and I sailed at sunset with Mason and Lynn and they are amazing people with a passion for sailing. Mason helped my young budding sailor to understand more about the sport and also let her be at the helm under his supervision. The vessel is in great condition and has all the amenities. They made sure we got great photos and memories. I would sail with them again and again!
- 5.0/5(3 Hour – Sunset Sail)
Outstanding sailing experience
Captain Mason and First Mate Lynne offered a very convenient pick up point next to the draw bridge in Woods Hole. From there, the experience got even better as they related their knowledge of the local harbor and surrounding waters. They have vast sailing experience and it shows. The boat is 42 ft, with sails and an engine. The navigational equipment is sophisticated. We were able to swim, eat a nice dinner, and watch the amazing sunset.
- 5.0/5(2 Hour – Family Fun (AM or PM) - 6:00 PM)
Amazing experience!
Captain John was awesome! My family had such a great time on thr water. He was very patient helping my kids fish for the first time and very knowledgeable about the fish we caught (they were plentiful) and the surrounding area. We will definitely book with him again the next time we are here. Highly, highly recommend booking a trip with him. It’s been the highlight of our trip so far!
- 5.0/5(2 Hour – Family Fun (AM or PM) - 10:00 AM)
Great fishing trip!
John's boat was exceptionally clean and organized. My girls enjoyed learning to fish. John is very friendly and makes fishing fun for the family.
