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Chesapeake Bay Tall Ship Sailing Vacation...

Sailing Cruises from Baltimore, MDChesapeake Windjammer Cruises...

Liberty Clipper sailing vacations start from Fells Point, an historic seaport in Baltimore's Inner Harbor. You're invited to board the ship anytime after 4pm on the day before the scheduled departure. While in Fells Point, we recommend you view the USS Constellation, one of America's first warships, stroll cobblestone streets and settle into the ship to meet your fellow passengers. The ship will set sail the following morning reaching out towards the Chesapeake sailing under the battlements of Fort McHenry, which inspired Francis Scott Key's composition of our National Anthem, and cruise down the bay before stopping at any number of our ports of call on your sailing cruise.


Chesapeake Bay Sailing Cruise Crab Boil Feast


Depending upon which windjammer cruise you select you may visit Annapolis, MD, home to the United States Naval Academy, Saint Michaels on the Eastern shore of the Chesapeake or any number of coastal hamlets. In addition to daily home-cooked meals, each Chesapeake Windjammer Cruise will include a traditional Chesapeake Bay Crab Boil. Each windjammer cruise is different – while some of our sailing vacations have more specific itineraries, on many of our relaxing trips, we will plot the course depending upon the weather and whatever fun events may be happening at the time.


Chesapeake Bay Windjammer Cruises - Lighthouse Viewing




Your sailing cruise may find that the Liberty Clipper sails for Solomon’s Island on the Western shore of the Chesapeake Bay or we may head across to Saint Michaels on the eastern shore. St. Michaels was explored by Europeans as early as 1524 and was once an important shipbuilding city. Today, St. Michaels boasts that author James Michener called this city home while researching and writing his book Chesapeake. This town is now a favorite for its history, scenic buildings and shopping.


Chesapeake Bay Sailing Cruise Vacations to St. Michaels


The Chesapeake Bay boasts some of the world’s finest protected sailing.  We hope you will join us as our guest aboard the Liberty Clipper for a relaxing and recharging sailing vacation.  We’ll provide you with amazing food, small boats to sail, and help you explore all the Chesapeake Bay has to offer…  This close to home sailing vacation will help you explore the history of the region while you enjoy yourself on a sailing ship where you are even invited to steer the ship!



Other windjammer cruise highlights...

While on your windjammer cruise, you'll have the opportunity to explore ashore each day on a different island. Our crew is here to help you have a memorable sailing vacation. You may avail yourself of our:

  • Rowing and sailing boats
  • Inflatable sea kayaks
  • Rope swing off the masts
  • Hammocks
  • Beach towels

Chesapeake Bay Windjammer Cruise Itineraries...

Our tall ships ply the waters of New England in the summer months from June through September. We have an exciting lineup of sailing vacations as follows:

  • Great Chesapeake Bay Schooner Race Cruise: 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.
  • New York City to Baltimore Sail: Sail from New York City to Baltimore, MD every fall on an adventure sailing cruise aboard our classic tall ship!

We also offer New England Sailing Vacation Cruises as follows:

  • Gloucester Schooner Race Cruise: Sail from Boston to Gloucester, MA and compete in the annual Gloucester Schooner Race! You'll love sailing off the coast of Massachusetts in company with other tall ships for this exciting sailing vacation. Every Labor Day Weekend!
  • Islands of New England Cruise: Sail from Boston to New York City aboard a classic tall ship. Explore coastal New England on this discover cruise from Boston to New York City!


We also offer special repositioning cruises each year as we move our ships from New England to the Caribbean. These are offshore sailing cruises where you'll be welcome to help join the crew in the sailing of the ship on these repositioning cruises.

  • Northbound Repositioning Cruise: Sail north from the Caribbean each May on an offshore adventure sailing cruise!
  • Southbound Repositioning Cruise: Sail southbound from New England to the Caribbean on a classic tall ship!

Please review our Windjammer Cruise Schedule for more information about or scheduled tall ship cruises and to learn about the specific itineraries available.  We welcome you to learn more about our sailing ships LIBERTY CLIPPER and LIBERTY STAR for more information or view our Windjammer Cruise Photo Gallery.

Chart your Course on a Chesapeake Bay Windjammer Cruises