Boston Harbor Sailing Cruises & Tall Ship Windjammer Cruises!
Tall Ship Windjammer Cruise Sailing Vacations...
Liberty Fleet of Tall Ships offers 3- to 6-day Tall Ship Windjammer Cruises aboard the majestic Schooner Liberty Clipper, a 125-foot historic replica of an 18th century clipper ship.

Cruise the Coast of New England in May and September where we sail from Boston, Massachusetts.
Explore the history of the Chesapeake Bay in October and November where we sail from Baltimore, Maryland.
Cruise the Eastern Bahamas Out Islands in December through April from Nassau.
Special Cruises: Jimmy Buffett Tribute Cruise, Pirates of the Caribbean, Naturalist Cruise, Valentine's Day and Coastal Navigation & Sail Training!
Come experience the romance of a traditional sailing ship while enjoying modern comforts and amenities. Our chef prepares your meals with fresh local ingredients daily and each trip includes a Chesapeake Bay Crab Boil or a Caribbean Lobster Bake.
Watch dolphins jump in our wake, enjoy moonlit evenings at anchor or explore the coastal towns and villages we will visit. With just 28 passengers, you can always find a quiet place to yourself on our stately vessel. For the adventurous type, you can join in hoisting the sails, or just sit back and relax as our professional crew will ensure your safety and comfort.
Boston Harbor Sailing Cruises...
The Tall Ship Schooner Liberty Clipper provides Boston Harbor sailing cruises daily on a traditional schooner from June through September. Sail on our tall ship on a regularly scheduled harbor cruise or charter the whole ship for your special event:
- Daily Harbor Sailing Cruises
- Boston Tea Party Reenactment Sails
- Sunday Brunch Sails
- Corporate Charters
- Weddings & Private Events
- Liberty Classroom
- Special Events
Welcome aboard!
Dolphins dance under the bow...

Sailing a Tall Ship...
