Choose your Sail!
- MOST POPULAR!
Scheduled regularly throughout the season, the Alabama sets sail from the Black Dog Wharf on three-hour long cruises. Join us onboard for an unforgettable afternoon or evening sail, help the crew in the raising of the sails, manning the wheel with the captain or just relaxing!
- All Ages
- 3 Hours
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!
"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
"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
"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
"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
"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