Authentic Boston Sailing Tours on Historic Boston Harbor
Small-group sails from Courthouse Docks — sunset, half-day, and full-day island adventures with BYO food and music.
Featured Sailing Trips
Choose from half-day, two-hour, or full-day sails exploring Boston Harbor and nearby islands.
About Boston Sailing Tours
Boston Sailing Tours operates sailing excursions out of Boston, Massachusetts, offering a range of guided and hands-on experiences on Boston Harbor. The company runs three primary trips: a 4-hour "Half-Day Sail Around The Islands" departing from Courthouse Docks that sails along the New England coastline and past historic stone fortresses; a flexible "2-Hour Day/Sunset/Night Sail" for short scenic cruises that showcase landmarks like the USS Constitution and Castle Island; and a 6-hour "Full Day Sailing & Island Experience" that visits Grape, Lovells, and Bumpkin Islands with time ashore to explore beaches, wildlife, and military remnants.
All advertised trips allow guests to bring their own food, drinks, and music aboard. The Half-Day Sail specifically notes a traditional cutter ketch as the sailing vessel and offers opportunities for guests to take the helm. Departure point for at least one listed trip is Courthouse Docks in Boston. The full-day itinerary includes landing at seldom-visited islands for wildlife viewing and beach time. Trips vary in length to suit short outings and extended island exploration.
Boston Sailing Tours markets these experiences to visitors and locals seeking scenic views of Boston Harbor, historical coastal sites, and island access without a long ferry. Trip details and durations are provided so prospective customers can select the sail that best fits their timing and interests.
Book a Boston Harbor Sail Today
Reserve a 2-hour, half-day, or full-day trip from Courthouse Docks — limited seats per sail, book early.