Boston Sailing

Discover top sailing tours in Boston, including harbor cruises, sunset sails, and scenic tall ship experiences. Book your Boston sailing adventure today!

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Boston Harbor Sunset Sail Tour

Experience a beautiful Boston Harbor sunset sail on the water and see some of the city's waterfront landmarks as the sun dips below the horizon. This elegant sa

★ 4.8 (190)

From $82.27 USD

Classic Tall Ship Cruise in Boston Harbor

Come out for a day sail adventure in Boston Harbor aboard one of our classic wooden schooners, Liberty Star or Fame. Get away from the hustle and bustle of the

★ 4.7 (807)

From $39.55 USD

Sightseeing Day Sail around Boston Harbor

Choose between either a 1.5 or 2-hour sail around Boston Harbor aboard one of our beautiful schooner Adirondack sailboats! These classic boats are reminiscent o

★ 4.8 (647)

From $54.44 USD

Sunset Sailing Cruise on a Tall Ship in Boston Harbor

If Boston is best seen from the water, then by far the best time to see it is during a sunset cruise on a classic Boston tall ship! We depart Fan Pier Marina an

★ 4.6 (498)

From $71.35 USD