Welcome Aboard!

Public and Private Sailing Cruises on the Chesapeake Bay on the Schooner Woodwind

Join us on our two beautiful, wooden, 74-foot schooners, Woodwind and Woodwind II, for a true sailing experience in Annapolis, Maryland.


October Sailing ScheduleLocated 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!


Champagne Brunch on the Woodwind

Cheer on the Schooners in the Chesapeake Bay Race

Contract of Carriage

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