Windjammer Sailing Vacation Cruises

Experience the excitement and fascination of windjammer barefoot sailing from our fleet of tall ships, we offer barefoot windjammer style cruising under sail from New England to the Caribbean. Our windjammer cruising destinations include the Out Islands of the Bahamas, the Caribbean Islands of the US and British Virgin Islands and the picturesque New England and mid-Atlantic coast lines. We also offer offshore adventure sailing crusies and Schooner Races! Whatever your speed, you're sure to discover something different on a barefoot sailing vacation cruise with the Liberty Fleet of Tall Ships.


Sail the Bahamas with the Liberty Clipper on a windjammer cruise sailing vacation!

Bahamas Windjammer Cruises

Set sail aboard the SCHOONER LIBERTY CLIPPER for an unforgettable sailing adventure on a Bahamas Windjammer Cruise! Come explore the Out Islands such as Eleuthera and the Exumas as we island hop from day to day. You'll be welcomed aboard by our expert crew who are there for your safety and enjoyment. From our qualified Captains to our wonderful cooks, they are there to make your windjammer cruise fun and memorable!



virginislands sailing

Virgin Islands Windjammer Cruises

Join us aboard the LIBERTY STAR for a Virgin Islands Windjammer cruise where you'll discover secret parts of the US and British Virgin Islands from our sailing ship. Each day, we will set sail for a new destination and a new adventure. Join us for a week of island hopping from fantastic beaches to famous watering holes and historic ports that can only be found sailing in the Virgin Islands!



Windjammer Cruise Sailing Vacations aboard the Schooner Liberty Clipper

Offshore Adventure Cruises

Sail with the LIBERTY CLIPPER for our most adventurous sailing cruises as we transit offshore from the East Coast to the Bahamas and back. You'll have a once in a lifetime opportunity to join the crew and help sail a working tall ship offshore! These cruises sail for mulitple days out of sight of land, and we usually try to catch a meal or two along the way. Space is limited and goes fast!



Windjammer Cruise Sailing Vacations with the Schooner Liberty Clipper

Islands of New England and Chesapeake Bay Sailing

A New England tall ship cruise aboard the majestic LIBERTY CLIPPER offers you the opportunity to explore the beautiful coast of New England by sea. Come join us for a memorable sailing vacation cruise in a world renowned sailing destination and discover all that coastal New England has to offer. Along the way she's likely to sail by and even stop at some of New England's iconic islands such as Nantucket and Martha's Vineyard. From offshore schooner races to island cruises and coastal voyages, we've got a sailing cruise for everyone!



Join the Liberty Clipper and dozens of other tall ships for the annual Chesapeake Bay Schooner Race!

Chesapeake Bay Schooner Race

Sail from Baltimore, MD to Portsmouth, VA aboard the LIBERTY CLIPPER in the Great Chesapeake Bay Schooner Race. This annual race event is held in mid-October each year. This is an exciting tall ship race with special crew parties (you're invited!) at each end of the race. You'll experience the thrill of racing amidst a fleet of over 50 tall ships! In 2012, the LIBERTY CLIPPER sailed at 14.7 knots and set a new ship speed record! This was done while sailing past the mouth of the Potomac River - what a thrill it was! This cruise is a favorite and space is limited so book your spot now for this historic race down the Chesapeake.



Join the Liberty Clipper in Gloucester over Labor Day Weekend for the Gloucester Schooner Race

Gloucester Schooner Race

Set sail on the Liberty Clipper for the Gloucester Schooner Race and Schooner Festival on Labor Day Weekend! Gloucester is a wonderful seaport village steeped in maritime history and lore. In 2014, over 20 schooners plied the waters off of Cape Ann, Massachusetts during this annual gathering of tall ships. This weekend of special sailing events is an annual favorite and space is limited, so book today!