Day & Sunset Sails Martha’s Vineyard

Sail Marthas Vineyard

The ultimate way to enjoy the surrounding beauty of Martha’s Vineyard – an afternoon or sunset sail onboard the Black Dog Tall Ships.

Scheduled regularly throughout the season, the Black Dog Tall Ships set sail from the Black Dog Wharf on three-hour long cruises. Join us onboard for an unforgettable afternoon or evening sail, where as a passenger you join the crew in the raising of the sails, manning the wheel with the captain or simply sitting back, enjoying the gorgeous scenery as you sip a glass of wine. A sail onboard will be the highlight of your stay on the island. This is a true sailing experience, taking advantage of the World’s best cruising waters. Perfect for couples, both small and large groups, and families!

2020 Schedule & Rates:

  • Through August 14th: 1:00pm – 4:00pm & 5:00pm – 8:00pm
  • August 15th through Labor Day: 12:30pm – 3:30pm & 4:30pm – 7:30pm
  • Post Labor Day: Noon – 3:00pm & 4:00pm – 7:00pm
  • $80 per adult. $50 per passenger under 12 years old. Children 3 years and younger sail for free unless sail is sold out!
  • Group discounts available for parties 10 and larger.
  • Waters, soda waters & cheese platter provided.
  • BYOB and picnic meals are welcome.
  • Day sailing passenger capacity: Shenandoah – 35 passengers | Alabama – 49 passengers