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Boston to New York

Example 7 Day Cruise aboard Liberty Clipper
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Scout the islands of New England on this 7-day island hopping coastal sailing voyage from Boston to New York. This trip mixes the best of laid back barefoot style cruises with a little adventure. Take a stroll through historic Faneuil Hall or head over to the north end for a taste of Little Italy in Boston. The Liberty Clipper sails south along New England, stopping at various small coastal towns where you can explore and head ashore. Visit locations such as Nantucket, Martha's Vineyard, Cuttyhunk, Block Island, and Long Island - all of this and more on this unique cruise en route to New York City.

Day-by-Day Summary

Day 1 : Boston | Embark
Days 2-6 : Sailing the Atlantic Coastline
Day 7 : New York City | Disembark


  • Visit Nantucket's Great Point Light, a lighthouse first built in 1784
  • Explore Martha's Vineyard, a longtime New England summer colony
  • Relax at Cuttyhunk Island, located between Buzzard's Bay and Vineyard Sound
  • Taste some unique wines at Long Island's famous vineyards


Liberty Clipper

Places Visited


Trip Type

  • Small Ship

Activity Level


Trip Snapshots

Lighthouse Exploring town The Clipper in the harbor Caribbean feast Lighthouse on the shore

Day 1 Boston | Embark

Embark the Liberty Clipper between 12pm and 4pm in Boston, Massachusetts. Settle into your cabin and enjoy a meal ashore in one of Boston's many historic waterfront area restaurants. Take a stroll through historic Faneuil Hall. Your New England Island Exploration sailing vacation on a tall ship starts here!

Day 2-6 Sailing the Atlantic Coastline

  • Ship
  • 5 Breakfasts, 5 Lunches, 5 Dinners
Sail out of Boston Harbor with the city skyline as a backdrop, a romantic start to an amazing coastal sailing vacation on a majestic tall ship. Experience the grandeur of Boston's historic sailing past aboard the Schooner Liberty Clipper.

Plan to have a breakfast in the Cape Cod Canal while transiting this man-made canal on Sunday morning. After the ship has passed under three bridges, the crew fires a cannon in salute to the Massachusetts Maritime Academy. Enjoy homemade meals from your Chef each day. Make stops along the way south where you can head ashore and explore. Each trip is unique and your captain chooses your ports by the wind and weather.

The Liberty Clipper follows sails southwards along New England stopping at various islands and small coastal towns. You may visit Nantucket, Martha's Vineyard, Cuttyhunk, Block Island, Long Island, or any other combination of coastal ports on the way to NYC.

Day 7 New York City | Disembark

  • 1 Breakfast
Arrive in New York City by mid-day. Disembark for your continued journey home.

Liberty Clipper

Per person starting at
Relax in your comfortable room aboard the Liberty Clipper.
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Standard Cabin
4 comfortable cabins with upper and lower bunks, vanity with hot/cold water, shared bath facilities.
Liberty Clipper's Shared bath cabin.
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Premium Cabin
3 comfortable cabin with lower bunk and double upper bunk, vanity with hot/cold water, and shared bath facilities.
The private cabin aboard the Liberty Clipper.
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Private Bath
5 comfortable cabins with a double lower bunks which feature a private bath.


All rates are per person based on double occupancy. A select number of premium cabins are available for an additional fee.

Singles can opt for willing to share at the same rate, or a single supplement of 50%.

Cruise fares do not include port taxes, an additional 5% of total cost.

Rate Includes
  • 1 bunk space in a standard double-occupancy cabin
  • All meals for the duration of your trip* Excluding Sunday night dinner
  • Coffee, tea, and juice (unlimited)
Note: bottled water, soda, and alcoholic beverages are not included and may be purchased separately on board, or consider one of our Drink Passes.
  • All linens – sheets, blankets, bath towels, beach towels, pillows
  • Use of all on-board water toys, such as snorkeling gear, kayaks, paddleboards, etc
  • Port fees (calculated as tax)
Rates Excludes
  • Travel expenses (Airfare, train tickets, taxi fare, etc) to/from the vessel boarding or disembarking locations
  • Hotel stays prior to or following cruise
  • Meals prior to or following cruise
  • Travel Insurance
  • Personal expenses such as souvenirs
  • Meals taken in place of those provided on board
  • Crew Gratuity – Our crew works very hard throughout your trip, and gratuities are always greatly appreciated. At the end of your trip you will have the opportunity to add this on to your cruise - we accept both cash and credit card on board. 15% of total cruise cost is recommended.


  • 6 Breakfasts, 5 Lunches, 5 Dinners
Payment & Cancellation Policies
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