We offer the finest Boston harbor cruise sailing trips in Boston Harbor aboard our fleet of tall ships. Come take the helm and see Boston's skyline and Boston harbor islands on a Boston Harbor cruise sail. Choose your Boston Sailing Experience:
We offer barefoot style tall ship Windjammer Cruises in New England, the Chesapeake Bay and the Caribbean Islands aboard our historic replica windjammers. Enjoy a Bahamas Windjammer Cruise or a Virgin Islands Windjammer Cruise.
Boston Harbor Sailing
A Liberty Fleet charter is unlike any other - enjoy a corporate outing with a sunset over the Boston skyline, or an afternoon sail with your closest friends. Team building programs available!
Sing along to traditional sea shanties, enjoy rum tastings and sample the sailor's favorite drink, the Dark and Stormy! Departs 8:30 PM on Saturdays on the Liberty Clipper (21+ only).
Looking for adventure, stay on a schooner in Boston Harbor. Our "hostel" style accommodations are more like "camping on the water." A rustic, unique and adventurous way to extend your Boston schooner experience.