Had a good time on a private sailing tour around the vineyard with Capitan Wendy! This is one of…read morethe options (we sailed with four different companies) on the island and this was the first! She's fantastic and friendly and kid-friendly as well! I would recommend a sail with her if you're on the island!

Really disappointed. The sailing part was wonderful but we had purchased a JAWS adventure. we were…read moresupposed to see different locations where the filming had happened. We never left the harbor! They didn't have any facts or plans to make this a JAWS cruise. we paid a lot of money for my husband's birthday. And when I wrote them- they never wrote back. Don't do the JAWS cruise.

Awesome sunset sail! Great attention to detail and very knowledgeable and fun guides. Thank you!read more

From the owner: Custom itinerary sailboat charters designed for your group's interests , skill level, and…read morepreferences. Contact us to discuss your ideal day on a beautiful 42 foot fully equipped sailboat.

Captain Jo was great this past weekend with our bachelorette party! He is highly experienced and…read morefriendly. Took many pictures for us and had waters and nice comfy furniture! We had so much fun.

Captain JoJo couldn't have provided better service for our sunset cruise. He worked hard to ensure…read morethe cruise fit exactly what we were looking for. We could play our own music, drink our own drinks and eat our own food all while he educated us in the ways of the water and the history of MV. Would recommend for any type of event/party. Jumping into the water in Lake Tashmoo was my highlight!

We had a GREAT time sailing on Ishmael when we were on the Vineyard. The boat is an old, true…read morewooden schooner built in 1929, so it's beautiful and has a lot of character. Captain Fred was so much fun (kind of a character himself!) and he's really knowledgable and indulged all my questions, telling me about how the boat works and teaching us a lot. We sailed from Vineyard Haven around Oak Bluffs and then moored near State Beach so we could all jump off the boat and go swimming. We had lunch on the boat and then sailed back. I highly recommend Ishmael for anyone who wants a unique, and genuine experience. Since the boat is privately owned, there is nothing commercial about it and you get a real sense of sailing the way the locals do it. And if there's good wind, there is nothing like skimming through the waves, feeling the spray of the ocean, as you take in the beautiful view.

From the owner: Intimate sailing experience on a vintage schooner built in 1929. Amazing perspectives of the island…read moreand adjacent water that can't be seen from the road!

Captain Lynne is extremely knowledgeable & made our night very memorable! We did a sunset sail & it…read morewas the highlight of our Anniversary trip! I highly recommend!

My wife, two daughters and I had an amazing time with Captain Lynne sailing the Sound. She is very…read morewelcoming and allowed me to help sail the boat. We returned a little early so we could jump off the boat and swim in Lake Tashmoo, which our daughters especially enjoyed. Also, Ena is a beautiful classic wooden boat with a mahogany hull and trim and spruce mast and boom. Tough to maintain but beautiful to sail!

We had a wonderful harbor cruise and tour with Captain Dave. The boat provided a smooth ride, the…read morecaptain was friendly and informative, and the crew was very pleasant. Captain Dave even gave way for our 2 young granddaughters to take the helm.

Gus is great!! We had the best time on a bachelorette trip to Martha's Vineyard. Highly recommend!read more

I went on a fantastic full day private sailing charter from Mattapoisett. We got to sail across the…read morebay to Woods Hole, Hadley Harbor and Eel Pond. Georgeous day, beautiful well equiped boat and very professional captains that know the area very well. I will definitly be making this an annual occasion and might even be back to take lessons.

From the owner: Our Passion Charter Company offers custom sailing charters out of a variety of different ports…read moredepending on the time of year and the location of our 42 foot sailing vessel 'Our Passion'. During the summer and early fall we offer charters in the waters of Buzzards Bay and Vineyard Sound. Come late fall we will begin to take 'Our Passion' south, stopping in various ports of call to offer charters in areas such as Annapolis Maryland, Norfolk Virginia, Charleston South Carolina, and West Palm Beach Florida. Please contact us to inquire about our location and availability for charter.

Amazing service! Captain Ed is truly a great guy! Made the day so enjoyable and relaxing. We have…read morebeen coming to MV for many years and have never seen the island like this! We will definitely be booking next summer for sure

From the owner: Book your own private charter on Martha's Vineyard's only Powerboat Day Sail. Our 20th season !…read more Relaxing sun and fun cruising for 1-6 people. Clothing Optional Itineraries to Gay Head available