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Welcome Aboard!

Our Season will be opening on Saturday, June 6 with very limited capacity.  We have updated all the changes in the red banner above. We are so excited to sail with you again!

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!

  • 2 Hour Public Sailing Cruises
    2 Hour Public Sailing Cruises
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  • Specialty Cruise Calendar
    Specialty Cruise Calendar
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  • Guests with sunglasses and smiles enjoying glasses of wine on the boat
    Private Sailing Cruises
    Private Sailing Cruises
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  • Schooner Woodwind Gift Certificates
    Schooner Woodwind Gift Certificates
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  • Sunset Sails
    Sunset Sails
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Make your sailing experience a memorable one! Sail away with us!

Sailing Season starts April 2020.

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Schooner Woodwind
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