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

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!

  • Our two beautiful, wooden 74-foot schooners, Woodwind and Woodwind II, offer and unparalleled sailing experience in Annapolis, Maryland.
    2 Hour Public Sailing Cruises
    2 Hour Public Sailing Cruises
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  • Specialty Cruise Calendar
    Specialty Cruise Calendar
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  • Sailing Cruises: October 5-9 from the U.S. Sailboat Show
    Sailing Cruises: October 5-9 from the U.S. Sailboat Show
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  • Enjoy the beautiful views as part of your corporate teambuilding event.
    Private Sailing Cruises
    Private Sailing Cruises
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  • Sunset Sails
    Sunset Sails
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  • Team Building
    Team Building
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  • Multi-Day Cruises
    Multi-Day Cruises
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  • We educate girl scouts about the
    Student Cruises
    Student Cruises
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  • Schooner Racing
    Schooner Racing
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Make your sailing experience a memorable one! Sail away with us!

Sailing Season starts April 15, 2017.

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