Transit Cruises and Tall Ship Races
Join the Liberty Fleet for a Tall Ship Sailing Cruise along the Atlantic Coast. We offer overnight sailing vacation cruises in New England 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, and enjoy life out of sight of land. These are our most adventurous sailing trips.
Select a Most Popular Cruise, Search by Date, or learn more about the different cruises below.
Most Popular Cruises
Boston to New York City Cruise
Come join the LIBERTY CLIPPER for a coastal sailing vacation on a tall ship from Boston to New York and…
Come join the LIBERTY CLIPPER for a coastal sailing vacation on a tall ship from Boston to New York and explore the Islands of New England!
Gloucester Schooner Race (Labor Day Weekend)
Boston → Gloucester → Boston | Starting at $125 per leg
The famous Gloucester Schooner Race! Book now to sail from Boston to Gloucester or back, and even book a spot on the boat for race day! You won't forget this exhilarating experience!
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All Transit Cruises & Races
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!
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.
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.
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 the whole weekend, or book single legs of the journey (even sail with us during the race on Sunday)! You’re welcome to help the crew race the ship, or just relax, enjoy a book, feast on our great meals and BBQ! Please check back in the Spring of 2019 for Labor Day Weekend 2019 dates.