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Liberty Fleet of Tall Ships

Boston Schooner Sailing and Boston Harbor Tours

Boston Harbor Sailing

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:
liberty fleet windjammer cruises n

Windjammer Cruises

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

Boston Harbor Sailing Charters & Private Event Sails

Boston Harbor Private Events Sails

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!
Boston Sailing Trips on Schooners

Boston Harbor Sails

90 minute to 2 hour Boston harbor sail cruises departing six times daily on the Liberty Clipper and Liberty Star beginning at 10:30 AM.
Liberty Clipper Liberty Star

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Boston Harbor Sunset Cruise Sail

Boston Harbor Sunset Sails

Sunset cruises of Boston Harbor depart daily at 6:00 PM on the Liberty Clipper and 6:30 PM on the Liberty Star.
Liberty Clipper Liberty Star

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BOOK NOW

Boston Rum and Revelry Night Sail with Entertainment and Music

Rum and Revelry Night Sail

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).
Boston Sunday Brunch Sail on a Boston Harbor Boat

Sunday Brunch Harbor Sail

A family favorite! Help raise the sails and then enjoy a delicious Boston brunch on board the Liberty Clipper catered by the Silent Chef! Departs 11:00 AM on Sundays.
Boston Sunday Brunch Sail on a Boston Harbor Boat

Boston 4th of July Sailing Cruises

A variety of sails for the whole family. From our Kids Sail, Day Sails and Fireworks Sail, there are many ways to enjoy Boston Harbor this 4th of July!
Liberty Clipper FireWorks Liberty Star FireWorks

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BOOK NOW

Boston Harbor Sailing Charters & Private Event Sails

Boston Tall Ship Overnights

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.
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