Sail Martha’s Vineyard Aboard the Historic Schooner Alabama
Day sails, sunset cruises, and Oak Bluffs fireworks views departing from Tisbury, Massachusetts.
Featured Cruises & Day Sails
Choose from Day Sail, Sunset Sail, and the Oak Bluffs Fireworks Cruise aboard Schooner Alabama.
About Black Dog Tall Ships
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.
Reserve a Sail on Schooner Alabama
Book a Day Sail, three-hour Sunset Sail, or Oak Bluffs Fireworks Cruise — advance reservations recommended.