Chesapeake Bay Sailing Destinations

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.  Sail into the Bay on our New York City to Baltimore Mid-Atlantic Sailing Cruise, or join is for an exciting multi-day tall ship festival, the annual Great Chesapeake Bay Schooner Race!  This close to home sailing vacation will help you explore the history of the region while you enjoy yourself on a traditional tall ship.  Relax on deck or become part of the crew - you can even help man the helm and steer the ship!


Enjoy beautiful sunrises and sunsets offshore on a New York to Baltimore sailing cruise!

New York City to Baltimore
Mid-Atlantic Offshore Sailing Cruise

This 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. We will enjoy some wonderful sunrises and sunsets at sea and possibly even see whales and dolphins along the way. We try to catch at least one of our meals on the way and always have a blast on this trip into the Atlantic!


Join the Liberty Clipper and sail in the Great Chesapeake Bay Schooner Race!

Great Chesapeake Bay Schooner Race

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.