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Sailing Charters in
Annapolis, MD

Classic Sail Charters offers Chesapeake Bay sailing adventures on our thoroughly refined sailing yacht, the Licentia. It is exquisitely appointed, safe, and ready for you to call home while you enjoy the mystique and allure of some of the best sailing grounds in the world.

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1 - 6 People | 3-Hour (AM/PM) - 2.5-Hour (Sunset) Sailing Yacht Cruise | 25% Deposit

Minimum age: 7 years.

Gratuity not included in pricing







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Chesapeake Bay - Annapolis

Looking for a unique sailing experience on the Chesapeake Bay? Our charters are the perfect way to explore the Bay and its navigable rivers. As the largest estuary in the world, the Chesapeake Bay is a natural beauty filled with an abundance of wildlife. Create your own sailing adventure on the Chesapeake Bay as we work with you to define your perfect excursion and then you may leave the rest to us!

Annapolis, located less than an hour from Washington, D.C., is noted not only as the location of the US Naval Academy but as America’s ‘Sailing Capital.’ It is home to a rich history that includes the oldest working state capitol building in the U.S., noted as the location where General Washington resigned his commission, as well as dozens of first-class bed and breakfasts, hotels, and fantastic restaurants. As a sailing venue, it is second to none.