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Tall Ship Transit Cruises & Races

Join Us for a Tall Ship Sailing Cruise Along the Atlantic Coast!

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We offer overnight sailing vacation cruises in New England and along the Atlantic Seaboard for our offshore transit cruises. These exciting cruises offer something for everyone!

Each spring and fall, we reposition the Liberty Clipper between her winter and summer cruising grounds. These sailing adventures offer you an opportunity to sail a classic tall ship on a blue water passage, unlike most of our usual windjammer cruises. 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 popular cruise, search by date, or learn more about the different cruises below.

Spring Transit (Bahamas to Boston)


Racing (Boston)


Gloucester Schooner Race - Labor Day Weekend 2020

Every Labor Day Weekend, the Liberty Clipper offers a three-day round-trip sail 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, and feast on our great meals and BBQ! Please check back in the Spring of 2020 for Gloucester Schooner Race 2020 dates.

Liberty Fleet Schooner race

Fall Transits (Boston - NYC - Baltimore - Portsmouth VA)


Boston to New York City

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!

Boston Harbor tall ship

New York City to Baltimore

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 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 about.

New York City from the water

Chesapeake Bay Schooner Race

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 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.

Gloucester schooner race

2021 Northbound Transit

Join the Liberty Clipper and her crew for a northbound transit sail from where she spends the winter months in Nassau, BAH, back up to Boston, MA, to begin her summer sailing! This is a mostly offshore excursion, with the majority of time spent in open water as we sail across the Gulf Stream, while possibly making a few stops in such places as Charleston, SC, Newport, RI, and others! (All locations subject to change based on schedule, weather, etc. and are not guaranteed.)

northbound transit

*Please note we are unable to accept deposits for reservations made online. If you would like to make a reservation and put down only a 50% deposit, please call our office and we would be happy to help you. Some restrictions may apply. See Terms of Service for details.

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