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Top Boston Sailing Trips


Sightseeing Day Sail around Boston Harbor

clock 90 to 120 minutes
  • Choose between either a 1.5 or 2-hour sail around Boston Harbor aboard beautiful schooner Adirondack III, an 80-foot pilot schooner of the 1890s. Sail past the seaport district, Castle Island, Fort Independence, Spectacle Island, and Long Island with Long Island Head Light. Great for families and friends who want to sail and see the sights of...Read more

Boston Harbor Sunset Sail Tour

clock 2 hours
  • Experience a beautiful 2-hour Boston Harbor sunset sail on the water and see some of the city's waterfront landmarks as the sun dips below the horizon. You will be aboard the most elegant sailing yacht in town, Adirondack III, a classically styled, 80-foot pilot schooner. Adirondack III is the fastest and most elegant schooner in Boston Harbor....Read more