Adventure Collective
Water Activities & Historic Black Dog Tall Ships on Martha’s Vineyard - Vineyard Haven

Water Activities & Historic Black Dog Tall Ships on Martha’s Vineyard

Tisburyeasy

Difficulty

easy

Duration

4–5 hours

Fitness Level

Everyone should be in good health; minimal physical effort required for participation.

Overview

Sail aboard the historic Schooner Alabama off Martha’s Vineyard and experience maritime beauty and history firsthand. Join this memorable day trip for all ages.

Tisbury, Massachusetts

Day Sail

2 Hours • All Ages • Fills Fast, Book Now!

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About This Adventure

Experience the breathtaking beauty of Martha’s Vineyard aboard the historic Schooner Alabama. Join the crew in raising the sails or relax with a glass of wine as you cruise the stunning waters. This unique sailing adventure, perfect for all groups, promises unforgettable memories and a taste of maritime history.

The ultimate way to enjoy the surrounding beauty of Martha’s Vineyard is to sail onboard the Schooner Alabama.

Duration

2 Hours

About the Trip

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, 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!

What to Bring

  • Waters, soda waters & cheese platter provided.
  • BYOB and picnic meals are welcome.

Note on accessibility:

Due to her age and historic nature, our schooner ALABAMA is unfortunately not handicapped accessible. Boarding the ship requires climbing a short ladder from the water taxi. This, as well as deboarding is assisted by our crew but passengers should be comfortable with and able to climb in order to do so safely. Once onboard, in order to access the ship’s cabins below deck, including the bathrooms, passengers must once again use a stairwell-style ladder.

About The Schooner Alabama

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. She is not a replica, a ship built to emulate the style of past generations, but rather a design of Thomas F. McManus, a man widely regarded as the best designer of all the Gloucester fishing schooners. Alabama’s second phase of her life began when the Coastwise Packet Company and its owner, Robert Douglas purchased and brought her to Vineyard Haven in 1967. 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. The rebuild that was a result of this decision lasted over three years and replaced almost 90% of her original form. As with the Shenandoah, Captain Douglas gave every consideration to her construction and the result is a vessel true to the era and design of McManus. The fishing schooner was an American invention, and the Alabama represents the finest vessels from this area when ships like her were relied on to provide the country with the staple of its economy, codfish.

Captain Morgan H. Douglas

Captain Morgan H. Douglas, third eldest son of Captain Robert S. Douglas, has been skipper of the Alabama since the 2005 season. He has been sailing with his father on board the Shenandoah since birth and received his 100 ton U.S. Coast Guard Captain’s license in 1999. A graduate of Tabor Academy and Gettysburg College. He ia an avid sailor, surfer, kitesurfer.

Adventure Tips

Arrive early

Get ahead of the crowds to secure the best spot on the schooner.

Dress for the weather

Bring layered clothing and sun protection for a comfortable experience.

Participate actively

Help raise the sails or handle lines for a more immersive experience.

Bring water and snacks

Stay hydrated and keep energy levels up during the cruise.

Local Insights

Wildlife

  • Seagulls
  • Porpoises

History

The Alabama has been part of Martha’s Vineyard’s sailing community for decades, representing the classic New England schooner tradition.

Conservation

The operation emphasizes eco-friendly practices, such as minimized waste and marine preservation efforts.

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Adventure Hotspots in Vineyard Haven

Frequently Asked Questions

Recommended Gear

Sunglasses

Essential

Protect your eyes from the sun's glare on the water.

Wide-brim hat

Essential

Shield your face from sun exposure during the cruise.

Sunblock

Essential

Prevent sunburn while enjoying time on deck.

Layered clothing

Essential

Dress in layers to stay comfortable as temperatures fluctuate.