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.
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Difficulty
easy
Duration
3 hours
Fitness Level
Suitable for most ages and fitness levels, though boarding requires ability to climb ladders.
Wildlife
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.
Black Dog Tall Ships
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.
Black Dog Tall Ships is a Tisbury, Massachusetts–based sailing operator that runs signature excursions aboard the historic Schooner Alabama.
The company offers a range of public and private sails that showcase Martha’s Vineyard coastal scenery and maritime heritage. Day Sail cruises invite groups to join the crew in raising sails or relax on deck with a glass of wine while cruising Vineyard waters. The Sunset Sail is a three-hour outing tailored for couples and families seeking evening views and a relaxed onboard atmosphere. The Fireworks Cruise / Oak Bluffs departs for a sunset sail and anchors near the Oak Bluffs fireworks display; guests are encouraged to bring picnics and blankets for an unobstructed waterfront perspective.
Black Dog Tall Ships emphasizes accessible, memorable experiences suitable for a wide range of guests and group sizes. The vessel, Schooner Alabama, provides a historic platform for interpreting local seafaring traditions while delivering recreational sailing. Operations are based from Tisbury, making embarkation convenient for visitors staying on Martha’s Vineyard. Bookings typically cover single sails, seasonal events, and special occasion charters, offering flexible options for island visitors and residents. Safety procedures, crew-managed sail handling, and guided onboard routines support guest comfort during each voyage. Advance reservations are recommended during peak island season to secure preferred dates and group arrangements. Black Dog Tall Ships connects island visitors to classic New England sailing through curated daytime, sunset, and fireworks cruises that highlight coastal vistas, maritime history, and relaxed, social time on the water. Ideal for memorable island outings.
Location
Tisbury, MA
Sail from Martha’s Vineyard harbor
Vessel
Schooner Alabama
Historic schooner platform
Sunset Sail
3 hours
Three-hour evening cruise
Tours Offered
3
Day, Sunset, Fireworks cruises
Book a Day Sail, three-hour Sunset Sail, or Oak Bluffs Fireworks Cruise — advance reservations recommended.
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.
Windbreaker or Light Jacket
Protects against the cool, changing winds on the water.
spring
Sunscreen
Necessary to prevent sunburn during exposed afternoon or evening sails.
summer
Comfortable Non-Slip Shoes
Vital for safe boarding and movement on deck of the historic schooner.
Camera
Capture stunning sunset views and classic ship details.