Martha's Vineyard Historic Schooner Sailing Cruise

I’m a huge fan of boat tours, and this was easily one of the most memorable I’ve done. Sailing aboard the Alabama, a beautiful historic schooner celebrating its 100th anniversary in 2026, made the experience even more special. The three-hour sail is peaceful and scenic, with beautiful views of Martha’s Vineyard and across toward Falmouth. It’s not a heavily narrated tour—it’s really about relaxing, enjoying the sailing experience, and taking in the scenery. You can even help the crew raise the sails if you’d like. To board the Alabama, you first take a short, approximately two-minute ride in a small launch boat, and then transfer onto the schooner. Be sure to wear appropriate, comfortable shoes for boarding and moving around the boat. I also recommend bringing warm layers, especially for the end of the tour, when it can get chilly on the water. Guests are welcome to bring their own drinks and snacks. I brought a small rolling cooler and a bottle of champagne, which made the sunset sail even better. The crew was friendly, the boat was exceptionally clean, well maintained, and felt very safe. It’s not the least expensive activity on the island, but if it fits your budget, I absolutely recommend it. Sailing on such a beautiful piece of maritime history is a unique Martha’s Vineyard experience—and the photo opportunities are incredible.

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