This place is incredible. The perfect group of people running this place, most have been there for…read moreseveral seasons. I rented one of their 15 Ft sail boats here and took it out with my Girlfriend and we went right out and sailed the entire lagoon over the course of about 1.5 hours. The boat was in good shape and handled in the water well. The sail was in great shape too. The prices are very affordable and it took literally no time to get out on the water, they rig for you and send you off. The sailboats would fit 4 adults comfortably and the views in the lagoon are fantastic. Highly recommend this if you are in MV for any amount of time. I noticed they have good kayaks and other adventure options as well. 5 stars, thanks Winds Up !

Jeff is the man. We rent kayaks every year from Winds Up. We got in a late today and Jeff helped…read moreus out getting everything we needed. And reserving online was super easy.

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.

A great family run small business that will make you feel like old friends. We had a mixed group of…read morethose who had done this elsewhere and those new to it. Mark and his son made us feel at ease. After our parasailing we rented jet skis and spent an hour in the surf. A great way to spend some time on a warm day.

Simple online reservation, easy booking, very friendly employees, overall a quality experience…read more $300 for an hour including tip, but was a very memorable experience.

I'd give this 6 stars if I could. Perfectly executed, of the highest quality. Our MV vacations have…read morealways strictly involved sticking to beaches, hikes, sunsets, nature-related wholesome activities. But succumbing to this tourist attraction was just plain good for the soul. We had a large group with little ones ranging from ages 1-8, and some 40 y/o-ish adults who were child-sized and/or child-like at heart. This made for one of the best memories we've made on this island. There was something for everyone. The 1 yo was saying "Argh" by the end, the 3-5 yo's were thrilled to be in the action, and even my 8 yo who I thought may be slightly too old for it got into his "Salty Dog" character, and asked me at the end, "How did they coordinate something like this??" We adults were laughing the whole time. The crew was fantastic, and props to the newest pirate Riptide who would come check to see if the baby wanted to partake in the revelry ;) My sixth star is for the precision and attention to detail, going the extra mile (personalized kids' "pirate name" tags made in advance), good people all around. Each time you thought, this couldn't get better, they would one-up themselves.

Absolutely enthralling experience for our 3.5 year old this summer. Worth every penny (and then…read moresome)!

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!

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

Well organized and great time sailing one these two black dog tall ships. They do tours to keep the…read moreboat in shape. The Capitan is no nonsense and makes the able bodied guests work which is fantastic experience for kids learning to sail! This mama was able to sit back and relax while the boys learned the ropes (literally!) we would do this sail again!

We loved our sunset cruise and listening to the history of the Black Dog franchise. The son of the…read morefounder owner of the Black Dog Tavern explained the reason for the establishment of the tavern and the tall ship sailing programs. All proceeds for sailing go to maintaining the tall ship and staffing. I loved it. The crew made it fun they were nice and down to earth. Plus the group was small so it offered a level of intimacy that if fully sold out we wouldn't have experienced. We brought our dinner and drinks, enjoyed to views and sailed on a beautiful tall ship. It was the perfect ending to our Vineyard weekend.

The most experienced Captain on the East Coast. Sequoia will make your trip…read more safe, delightful and memorable. Comfortable and relaxing with a witty and charming crew to cater to your every need. Competence and seamanship reign supreme on this classic vessel!

Wonderful experience! Sequoia is a warm and welcoming…read morehost/captain. His sailboat, Tandemeer, is clean and spacious. We loved sleeping on the water.

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!

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!