Chesapeake Bay Tall Ship Windjammer Cruise Sailing Vacation...

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.

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.

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.

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!