They are one of the great sights of Summer on Martha’s Vineyard. The Black Dog Tall Ships sailing in and out of Vineyard Haven Harbor. The Douglas family owns and operates two of them — the Alabama, the 90-foot white schooner, and the black 108-foot Shenandoah.
Long before The Black Dog became an iconic brand known the world over, the Douglas family made their name sailing, right here on Martha’s Vineyard. And a generation later, they’re still at it. Sailing the tall ships, and of course, managing their well known brand, from Black Dog restaurants to apparel, on the Vineyard and elsewhere.
The ships sail out into Vineyard Sound, toward Cape Cod, with the adventure largely dictated by the wind. The views are incredible, but half the fun is being part of the fun. Guests help the crew raise the mammoth sails.
Our own Vineyard Bucket List adventurist, Guinevere Cramer, climbed aboard the Alabama and sailed off on this classic Vineyard experience.
One or both of the tall ships sail daily and at sunset, throughout the summer season. You can check the Black Dog Tall Ship schedule here. There are also special kids sailing program, sailing lessons, and more.
The Martha’s Vineyard Bucket List is our ongoing curated video collection of the best Martha’s Vineyard vacation experiences and first-hand travel adventures. From exploring the island by tall ship or biplane to touring its lighthouses to finding the best beach walks, sunsets, and farm to table adventures, there’s a lot to discover. Martha’s Vineyard Bucket List Collection.