Liberty Clipper: Chesapeake Windjammer Cruises.

Chesapeake Bay Tall Ship Sailing Vacation…

Liberty Clipper sailing vacations start from Fells Point in Baltimore’s Inner Harbor. You’re invited to board tChesapeake Bay Sailing Cruise Crab Boil Feasthe ship anytime after 4pm on the day before the scheduled departure. 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.

While on your windjammer cruise, you’ll have the opportunity to explore ashore each day on a different island.  You may avail yourself of

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

The Liberty Fleet of Tall Ships
67 Long Wharf
Boston, MA 02110

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Whether you want to have fun on a special event cruise or simply relax on the water, Chesapeake Bay cruises have something for everyone. Enjoy the bounty of the bay on a fishing trip with your family and friends. If family fun is what you seek, consider an exciting pirate cruise. You can also give your family a truly educational experience aboard a nearly exact replica of a British schooner.

Experienced sailors can book a bareboat charter, while those who wish someone else to do all the work can sail in comfort with a captain and crew.  There are many options to choose from, all of which result in a great time on the water.

Spending a day, an evening, or even a week, on the Chesapeake Bay is a unique experience. There are historical areas to visit, spectacular scenery to enjoy, and local cuisine to be savored. There is nowhere quite like the Bay!

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ImageThe schooner Sultana is an almost exact replica of a British schooner that patrolled the North American coast just prior to the American Revolution. Sultana, called the “Schoolship of the Chesapeake,” provides educational programs for more than 5,000 students each year.

Sultana  provides day-long educational programs for up to 32 participants as well as live-aboard programs for up to nine guests. Students travel back in time to the “Age of Sail” and participate in hands-on activities aboard the Sultana.

Sultana is based in Chestertown, Maryland.

Sultana Projects, Inc.
105 S. Cross Street
PO Box 524
Chestertown, MD 21620

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59-alabama--shenandoah-croppedLiberté is a 74 foot schooner with a capacity of 49. She also has music, and a full bar. Liberté spend the summer off Cape Cod, but is available for private charters on the Cheasapeake Bay in the spring and fall.

Her berth is alongside the Chart House Restaurant in the Eastport section of Annapolis on Spa Creek. Her captain describes the sights you’ll see as follows: “After a very brief motor away from the dock, we’ll begin to hoist sail in the shadow of the Naval Academy. We can either sail up the protected waters of the Severn River, with riverside mansions and grand lawns gracing the shore, or out on to the Chesapeake Bay. Out there, we go north to the Bay Bridge or south to historic Thomas Point Lighthouse. Along the way we’ll pass many other boats of all sizes and shapes.”

Email for more information

Captain Chris Tietje
Liberte, The Schooner
222 Severn Avenue Annapolis, MD 21403

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Arabella Cruise WindjammerThe windjammer Arabella is a 160′ tri-mast with 20 cabins, which feature private bathrooms, satellite TV, and individual climate control. She has teak decks , a hot water spa, and shaded cabana seating.

The Arabella winters in the Caribbean and summers in New England, but is available for 5 and 6 night cruises on the Chesapeake with stops in Annapolis, Cambridge and St. Michael’s.

She is available for private & corporate charters,  group outings, family reunions, weddings, and other special occasions.  Reservations may be made by telephone only: 800-395-1343. You may email mailing address, cell number, and food allergies to, then call with credit card number.

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Schooner Woodwind

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Annapolis Sailing Cruises features two beautiful, wooden, 74-foot schooners, Woodwind and Woodwind II that provide a variety of cruise options, including:

The company states, “Located in the heart of the Chesapeake Bay, Annapolis is ‘America’s  Sailing Capital.’ Help raise the sails, steer the boat, or simply sit back and relax as Woodwind sails from the historic Annapolis waterfront, past the Naval Academy and cruises into the Chesapeake Bay.  As a family business, we take great pride in making your sailing experience a memorable one. Our captains and crew are engaging and enthusiastic. Sail away with us!”

All cruises leave from the Annapolis Marriott Waterfront Hotel

For more information, contact the Schooner Woodwind at 80 Compromise Street, Annapolis, MD 21401,  410-263-7837,

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