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.
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Cruise Options
- Schedule of Events for Saturday, September 5
- Boarding: 8 a.m.: Boarding begins for our adventure. Enjoy coffee and breakfast on deck as we prepare the ship to get underway!
- Sailing!! 9 a.m. – 4 p.m.: The ship sails from Boston to Gloucester, MA. The ship sails out of Boston Harbor and passes Boston Light while making passage to the beautiful Cape Ann. On this leg of the cruise, you may see whales in Massachusetts Bay and will likely sail in the company of other schooners on their way to Gloucester for the 34th annual Gloucester Schooner Race.
- Lighted Boat Parade & Fireworks Cruise: The Liberty Clipper sails in Gloucester from 7:30 p.m. till approximately 10 p.m. to watch a lighted Parade of Sail and watch the fireworks! This part of the trip is only available to guests staying the whole weekend aboard.
- Schedule of Events for Sunday, September 6
- 8 – 8:30 a.m.: Boarding for race day cruise. We depart promptly at 8:45 a.m. to line up for the race!
- 9 a.m. – 4/5 p.m. (approx.): The Liberty Clipper competes in the 30th annual Mayor’s Cup racing in the coastal waters off of Cape Ann, against a large fleet of tall ships! Bring your camera – events like this present rare opportunities to get some great pictures of a fleet of tall ships pressing forward under sail!
- Race Day Guests Depart after race concludes
- Schedule of Events for Monday, September 7
- 8 a.m.: Begin boarding for southbound day cruise passengers.
- 9 a.m. – 4 p.m.: The ship sails from Gloucester, MA to Boston, MA. The ship sails out of Gloucester bound south for Boston. On this leg of the cruise, you may see whales in Massachusetts Bay and will likely sail in the company of other schooners on their way home from the 34th annual Gloucester Schooner Race. Hear the crew tell their stories of the race and crew parties ashore. Lunch will be provided aboard during this southbound sail.
- Schedule of Events for Saturday, September 5
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!
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Saturday, Oct. 3 – Thursday, Oct. 8 | From $799
Boarding is between 12 and 4 p.m. on the first day of the cruise at the ship’s berth by the New England Aquarium in Boston, MA. Settle into your cabin before we depart, and then consider taking a stroll through Historic Faneuil Hall or head over to the North End for a taste of Little Italy in Boston. Your New England island exploration coastal sailing vacation on a tall ship starts here!
That evening, we sail out of Boston Harbor and enjoy dinner on board with the city skyline as a backdrop – it’s a romantic start to an amazing coastal sailing vacation on a majestic tall ship. We’re bound for the Cape Cod Canal, where we plan to have breakfast while transiting this man-made canal on Sunday morning with the Cape on our port side. After the ship has passed under three bridges, we fire our cannon in salute to the Massachusetts Maritime Academy.
The Liberty Clipper follows the coast southwards along New England, stopping at various islands and small coastal towns where you can head ashore and explore as weather permits. Each trip is unique – we may visit Nantucket, Martha’s Vineyard, Cuttyhunk, Block Island, Long Island, or any other combination of coastal ports on the way to New York City! Please note, on our transit cruises, we reserve the right to make adjustments to the schedule and itinerary based upon weather and other factors. Come aboard the Liberty Clipper for an unforgettable sailing adventure from Boston to New York City!
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.
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Friday, Oct. 9 – Tuesday, Oct. 13 | From $649
Join us for one of our most adventurous sailing cruises where you participate in the sailing and navigation of the ship as we set “sea-watches” for a voyage down the coast. If you’ve been an armchair sailor and want to earn your stripes, or you’ve always dreamed of sailing offshore on a working sailing ship, this is the voyage for you!
Join the ship in New York City on Friday, October 11 at 5 p.m. You dine ashore in NYC for dinner and we may set sail this evening, weather dependent. Take in the beautiful views of the New York City skyline from the water as we depart for our sailing adventure!
From New York City, we sail down the New Jersey Coast and continue up the Delaware Bay, where we transit through the C&D Canal and may anchor in the Sassafras and mud flats of the North Chesapeake before continuing on toward Baltimore.
We aim to arrive on Tuesday, October 15 by 5 p.m. In Baltimore, you may choose to disembark, or stay aboard for the Great Chesapeake Bay Schooner Race! Please note: On our transit style cruises, we reserve the right to make adjustments to the itinerary and schedule based upon weather and other factors.
This New York City to Baltimore cruise mixes the best elements of our more relaxed “windjammer-style” cruises with an offshore element to bring you a vacation cruise that you will never forget. Please note that on this cruise, we do sail overnight and have a schedule to keep. We enjoy some wonderful sunrises and sunsets at sea, enjoy viewing the stars at night at sea, and possibly even see whales and dolphins. We try to catch at least one of our meals on the way and always have a blast on this trip into the Atlantic!
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.
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Wednesday, Oct. 14 – Sunday, Oct. 18 | From $899
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 Baltimore to Portsmouth cruise is a favorite and space is limited so book your spot now for this historic race down the Chesapeake aboard our classic ship.
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.)
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Sunday, May 17 2020 – Thursday, May 28 2020 | From $1,799
We will welcome our guests to stay aboard the evening we return to Boston (Thursday night, May 28), and we will recommend any travel plans home to be made for Friday, May 29 in the event the ship is delayed due to weather conditions coming up the coast.
This is our most adventurous sailing trip we offer, and while this type of trip may be suited best for people with some sailing experience, we do not require any prior experience to join. Offshore sailing could pose additional challenges, so our guests have to be agile and able to go with the flow, as weather may impact our voyage plan and timing back to Boston. During this trip, you can become a part of the crew and take part in sailing the ship such as raising sails, running lines and even taking turns at the helm with the captain! If you are looking for a unique offshore sailing adventure aboard an authentic tall ship, look no further than this exciting transit aboard the Liberty Clipper!
*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.