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
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:
Boston Harbor Sailing
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!
Boston Labor Day Weekend Sailing Cruises
A variety of sails for the whole family; while we run our normal schedule, we also offer a few holiday weekend trips: Boston Harbor Fireworks sail aboard the Libery Star on Saturday, Sept 3 at 8:15pm, and a Coastal BBQ Sail aboard Liberty Clipper one-way to/from Gloucester, MA to/from Boston, MA.
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 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.
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.
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).
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 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.