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The Black Dog Tall Ships

Sailing Charter on Martha's Vineyard, MA

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Choose your Sail!

Our Ship

The schooner Alabama is a living piece of America’s maritime history. Built in 1926 for the Mobile, Alabama Bar Pilots, she served until her retirement in 1966. Never fitted out as a sailing vessel by the Mobile Pilots, she was finally given this opportunity thirty years later when it was decided to put her back to work in 1994.

Visit The Black Dog Tavern

Full service, year-round waterfront dining in our legendary Tavern on Vineyard Haven Harbor.

Tie-up at The Black Dog Wharf

Services ranging from hourly tie-ups to long-term transient professional care and service.

Shop The Black Dog Brand

Out of one sailing Captain’s love for the sea, his island home, and of course, his dog, The Black Dog Brand was born.

See why our customers love sailing with us!

Black Dog Sail!

"Really awesome sail with a super cool captain and crew! The Alabama has a ton of character and she really made it an enjoyable experience :) Have a chowder at the inn with a beer and set sail!!!!!"

– Robert J. • TripAdvisor
Awesome Sail!

"My family had a wonderful time on the Alabama! The Captain and crew were so hospitable. We all helped hoist the sails and then enjoyed a beautiful relaxing sail. Do this while on the Vineyard, you won’t be disappointed!!"

– Nicole D. • TripAdvisor
Great for groups!

"Spent a great afternoon on the water with Capt. Douglas and the crew- highly recommend! Can’t believe it took us this long to take advantage of this local gem!"

– Peter W • TripAdvisor
Great cruise!

"Such a treat to get out on the Sound on a beautifully crafted Tall Ship for a fresh perspective of this special island! Knowledgeable & friendly crew engaged guests to the extent guests could choose."

– adiverdiehl • TripAdvisor
Fun windy ride!

"had a great outing on the Alabama with our family. it was rather windy but the crew handled it well — beautiful trip. we did byo which worked ni key. enjoyed nice conversations with the crew and with other guests. Recommend!"

– Janet • TripAdvisor