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 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!

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.

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.

What a great learning experience. Great sailing on a beautiful historic schooner. Crew was great…read moreand allowed us to work alongside them. Answered all our questions. Would recommend for any group. Included water and chips.

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.

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

Fabulous trip, so much fun. The crew does a great job keeping the kids engaged the whole time.read more