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Sunset Sail with Black Dog Tall Ships on Martha’s Vineyard - Boston

Sunset Sail with Black Dog Tall Ships on Martha’s Vineyard

Tisburyeasy

Difficulty

easy

Duration

3 hours

Fitness Level

Suitable for most ages and fitness levels, though boarding requires ability to climb ladders.

Overview

Step aboard the historic Schooner Alabama for a three-hour sail around Martha’s Vineyard. Whether helping raise sails or sipping wine at sunset, this experience blends maritime heritage with coastal beauty.

Tisbury, Massachusetts

Sunset Sail

3 Hours • All Ages • Most Popular!

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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 sails or relax with a glass of wine as you cruise the stunning waters. This three-hour adventure is perfect for couples and families, making it a memorable highlight of your island stay.

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

Duration

3 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 for Boarding

Plan to arrive at Black Dog Wharf at least 15 minutes before departure to accommodate boarding procedures on the historic schooner.

Dress in Layers

Coastal conditions can shift quickly, so bring layered clothing to stay comfortable through sun, wind, or cooler evenings.

Limited Accessibility

Boarding involves climbing a ladder from a water taxi, and below-deck access uses a stairwell ladder; guests should be comfortable with these conditions.

Bring a Camera

The changing light around sunset highlights the schooner’s classic lines and island views, perfect for photography enthusiasts.

Local Insights

Wildlife

  • Harbor seals
  • Great blue herons

History

The Alabama was originally built in 1926 as a fishing schooner, representing a key era in New England’s maritime industry.

Conservation

Black Dog Tall Ships emphasizes low-impact sailing experiences that preserve the island’s fragile coastal ecosystem.

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Frequently Asked Questions

Recommended Gear

Windbreaker or Light Jacket

Essential

Protects against the cool, changing winds on the water.

spring specific

Sunscreen

Essential

Necessary to prevent sunburn during exposed afternoon or evening sails.

summer specific

Comfortable Non-Slip Shoes

Essential

Vital for safe boarding and movement on deck of the historic schooner.

Camera

Capture stunning sunset views and classic ship details.