Liberty Fleet Special Event
Sails and Cruises

Check out some of our special cruises and events - you won't want to miss these!


Specialty Boston Harbor Sails

Labor Day Weekend Sailing  (2018 dates posted)

New England Coastal Day Sail

Boston Tall Ship Sailing2Set sail aboard the SCHOONER LIBERTY CLIPPER on an offshore sail with meals included during this labor day weekend! This one-way trip to/from Boston to Gloucester, MA or Gloucester to Boston will give you an opportunity to explore Massachusetts Bay outsite of Boston Harbor. We will likely sail in the company of other tall ships and Schooners, sometimes we even sight whales! This trip includes breakfast and a great lunch under sail! We have a cash bar aboard for bottled water, soda, and adult beverages. We board each trip at 7:30AM and sail promptly at 7:45AM. This is an exciting trip (we only have 12 spots available!). We hope you'll spend labor day weekend with us sailing. Please e-mail or call for any additional details.

Boston - Gloucester: Saturday, Sept 1, 2018.  Departs at 7:45am. $100. BOOK NOW

Gloucester - Boston: Monday, September 3, 2018. Departs at 7:45am. $100. BOOK NOW


Labor Day Weekend Fireworks Cruises - 2018 dates coming soon!

fireworks thumbnailJoin us for an epic sail to end the summer! Boston will celebrate Labor Day with an exciting " Battle of the Barges" fireworks display! Enjoy our cash bar on board as we watch a magnificent display of color bursting in Boston Harbor! Sailing will be limited on this trip so that we can best position the vessel to observe the fireworks. In the event the fireworks are cancelled or rained out, a company credit will be issued, no refunds.

Dates will be posted once the City of Boston lets us know the plan!

Liberty Star: DATES TBD.  8:30-10:30 pm. $60. BOOK NOW


Rum and Revelry Sails (2018 dates posted yohoho!)   

rum rev 02Join the Liberty Clipper on Saturday evenings for our "after hours" Rum and Revelry sail! You'll enjoy the sparkling lights of the Boston skyline while being regaled with traditional songs of the sea performed by professional actors on board our flagship schooner. Haul up the sails to a sea shanty and experience the sounds of times gone by as you sail on our grand tall ship.

Visit our bar to pick up our signature drink and the sailor's favorite - a Dark 'n' Stormy! - featuring Gosling's dark rum, ginger beer, and a twist of lime. We also serve a variety of other favorite rum drinks and snacks on board.

Sing along to the music while sailing Boston Harbor on this exciting sail.  Every summer Saturday evening from June 9, 2018 until September 15, 2018. 



Sunday Brunch Sails (2018 dates posted)

Enjoy a Sailing Sunday Brunch on the Liberty Clipper!Come aboard the Liberty Clipper on Sundays from June 10, 2018 until September 16, 2018, for an extended sailing excursion around Boston Harbor with a fantastic brunch catered by our long-time partners, The Silent Chef! You'll enjoy beautiful midday views of the Boston skyline while dining on a variety of brunch buffet offerings. We begin with a continental style breakfast with fresh fruit, breads, and pastries, then get ready to set sail! Once you've "hauled away" to get the sails up, get ready for the rest of the meal with a variety of quiches, ham, and other hot breakfast favorites! Vegetarian options are available each week. Also, those of age should be sure to stop by our bar for a mimosa or bloody mary!




July 4th HarborFest Events (2018 dates posted)

FireworksCelebrate America's Independence Day in the city considered to be the "birthplace of the Revolution"! Complete your tour of Boston's rich history with a harbor sail on an authentic tall ship sailing Boston Harbor. Throughout the week leading up to the 4th of July, we will be including a few extra specialty sails, including a Kid's Sail and rounding out the celebrations with our fantastic Fireworks Cruise!

Read More



Schooner Races - awesome opportunities in 2018.

Experience the excitement of sailing with dozens of other tall ships on a Schooner Race!

Gloucester Schooner Race Cruise (Labor Day Weekend)

Set sail on the Liberty Clipper for the Gloucester Schooner Race! Each Labor Day weekend dozens of schooners sail off Cape Ann, Massachusetts during this annual gathering of tall ships. Come aboard for the full 3-day round trip excursion from Boston, or join us in the historic seaport town of Gloucester the day of the race!



Great Chesapeake Bay Schooner Race Cruise (2018 DATES POSTED)

Sail from Baltimore, MD to Portsmouth, VA aboard a tall ship in the Great Chesapeake Schooner Race. This annual race event is held in mid-October each year. This is an exciting tall ship race with special crew parties (you're invited!) at each end of the race. Read more on the Windjammer Cruises section of our website.



Adventure Sailing Vacation Cruises

While Boston harbor is our home port, when the weather begins to turn cooler we turn our ships south toward the bright warm waters of the Bahamas. From the end of November through mid May you can sail with the Liberty Fleet on week long windjammer style sailing vacations! Starting in October, the Liberty Clipper begins making her way south with a few stops along the Atlantic Coast including New York City and Baltimore. Click on the links below for more information about these individual cruises, or visit our cruise website: Liberty Fleet Windjammer Cruises!

Sail on the Liberty Clipper or Liberty Star in the Bahamas and Virgin Islands!

Boston to New York City: Islands of New England Cruise

New York City to Baltimore: Adventure Sailing Cruise

Bahamas Tall Ship Cruises