Atlantic Coast Sailing Cruises

atlantic coast cruises 01Join the Liberty Fleet for a Tall Ship Sailing Cruise along the Atlantic Coast. We offer overnight sailing vacation cruises in New England, the Chesapeake Bay, and along the Atlantic Seaboard for our offshore repositioning cruises. These exciting cruises offer something for everyone: tall ship races, schooner race, island hopping adventures, offshore sailing or sail training.

Each spring and fall, we reposition our ships between their winter and summer cruising grounds. These sailing adventures offer our guests an opportunity to sail classic tall ships on a blue water passage. You'll join the crew in the operation of the ship, take the helm, navigate, stand a watch and enjoy life out of sight of land. These are our most adventurous sailing trips.

Please see our list of available cruises for more information.



Gloucester Schooner Race

Gloucester Schooner Race Labor Day Weekend Cruise from BostonGloucester Schooner Race Cruise. Every Labor Day Weekend, the Liberty Clipper offers a three-day Labor Day weekend sail round-trip from Boston to Gloucester, MA. On this cruise, we participate in the Gloucester Schooner Race. Join us for an exciting opportunity to sail a schooner in a tall ship race. You're welcome to help the crew race the ship, or just relax, enjoy a book, feast on our great meals and BBQ!


Boston to New York City

Liberty Clipper Sailing New England CoastBoston to New York City: The Islands of New England Cruise. The first week of October each year, we offer a one-way cruise from Boston to New York City. This is an island hopping coastal sail from Boston to New York. This trip mixes the best of our laid back barefoot style cruises with a little adventure of near coastal sailing!


New York City to Baltimore

Offshore Sailing Tall Ship CruisesNew York City to Baltimore Cruise. Mid-October each year, we offer a one-way cruise from New York City to Baltimore. This is an offshore adventure sailing cruise on our tall ship. We will sail out of sight of land along the New Jersey Coast from NYC down to the Delaware Bay Entrance. From there, we will transit the C&D Canal into the upper reaches of the Chesapeake Bay. This trip is perfect if you're looking to earn your sea-legs, get some navigation or sailing experience, or are curious about what life "offshore" is all aboard.


Great Chesapeake Bay Schooner Race Cruise

Chesapeake Bay Schooner RaceGreat Chesapeake Bay Schooner Race Cruise. Mid-October each year, we participate in the Great Chesapeake Bay Schooner Race. On this tall ship racing cruise, we will sail amongst a fleet of tall ships and schooners as we race from Baltimore, MD to Portsmouth, VA. This 127-mile race is is offered as part of a 5-day cruise that includes a parade of sail in Baltimore Harbor, a crew party in Baltimore, the schooner race and the awards ceremony with pig and oyster roast in Portsmouth, VA. Come join our crew as we look to earn another victory in the race.


Charleston to Nassau 


2 Sails BillowingCharleston to Nassau Cruise. Join us for the final leg of our southbound journey!  You'll have the opportunity to participate in the sailing and navigating of the ship as we venture down the Gulf Sream, around Hatteras, and into the Bahamas.  Don't forget, a valid passport is required for this trip!