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.

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

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!

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

great experience! thanks for all your thoughtful planning. we really appreciated your efforts…read more super nice crew. they made us feel very comfortable

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!

Steve is an excellent charter captain, and his skills as an instructor are outstanding! I hadn't…read moresailed in many years. I'm 68 now and wanted to start again I thought my old skills would be beyond rusty. Steve inspired confidence in me from the start! He had me feeling comfortable a feeling more confident in no time! Thanks Steve.

From the owner: Spend the day on Buzzards Bay. BBYC offers 2,4, and 6 hour sails from beautiful Mattapoisett,…read moreMassachusetts. We're conveniently located off I-195 about an hour from Boston and minutes from Cape Cod. Our fleet includes a Pearson 35 and a Dyer 29, so if you're looking for a sporty sail on the bay or a relaxing motor cruise on along shoreline, we offer a variety of itineraries to make your day memorable. Buzzards Bay Yacht Charters is your premier sailing excursion company for family outings, bachelor/bachelorette parties, corporate outings or romantic getaways. We also have an outstanding sailing school with courses ranging from beginning keelboat sailing to coastal cruising and bareboat charter certification programs.

I had bought the cruise as my husbands Christmas gift! it was a perfect night to investigate th…read moreElizabeth's Islands! Don was a fun and knowledgeable host. we learned a lot, laughed a lot and enjoyed every moment. thank you

Great "3 hour tour", Ooops I mean 1. Best part was the tour maxes at 6 and my wife and I were the…read moreonly 2 aboard. Learned a lot of interesting facts about the area.. The Elizabeth Islands are beautiful and a hidden jewel. We had a great time and would do it again. Worth every penny of the reasonable price! Check it out

Location at Martha's Vineyard Island Oak Bluff, and unlike the other offices at Nantucket and…read moreHyannis, this office is just a one room booth (though it can fit a lot of young people at a time). I kept missing it, as it was a crowded Friday afternoon, but then later realized that it is exactly where it needs to be: fronting the entrance to the dock where the ferry leaves. We were able to change our departure (to go back to Hyannis) from 8:40 pm to an earlier 6:10 pm on Friday, and there was no charge since we did it before the original time elapsed...we just needed to show them our original invoice. Unlike the other Hy-line offices, there is no indoor seating, but plenty to pass the time since right in the middle of a busy tourist area. By taking the earlier return, it was a different crowd...more older and a lot less crowded. We got back to Hyannis in under an hour, and offloaded pretty easily. There were shuttles waiting in the nearby road (to avoid the heavy congestion in the pickup area), and we got the last two seats. We got dropped off at Lot 8 offsite in 10 minutes, and were on our way. Probably wouldn't recommend trying to see both islands on the same day, but it can be done via Hy-Line.

If you are the kind of person that says it's not about the destination it's about the journey, take…read morethe time to go on the old ferry not the high speed. The staff is super relaxed and we felt very welcome the minute we stepped on board. They made us feel like we were locals. They have a fully stocked bar, several comfortable areas to sit, great views and a very smooth ride. Only reason for lack of 5 stars is the boat is a bit old. Not that there is anything wrong with that. Just not quite a five star experience.