VisitAnnapolis.org

The Woodwinds, Sailing into Spring

Bears aren't the only ones who hibernate throughout the winter. As soon as the birds begin to chirp and the flowers begin to blossom, the boats around Annapolis find their way out of their plastic shrink wrap and into the cold waters of the Chesapeake Bay. The Woodwinds are 74-foot schooners…

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Annapolis Up Rigging Festival

There's a new festival in town May 13-15, 2022, the Annapolis Up Rigging! The 3-day event aims to highlight the Annapolis region's maritime history and its connection to the water with music, nautical arts, and of course, Tall Ships! Learn more about this inaugural festival on the Annapolis…

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Cruisers University

Summer is right around the corner, and soon it will be time to set sail. We know cruising the beautiful blue waters of the Chesapeake is the ultimate way to spend your summer days. Never sailed before? Want to learn something new or need a refresher in marine weather forecasting? Cruisers…

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Seas the Bay, Private Sailing Charters

The wind is blowing out of the south east, the motor is off and the sails are full as you head toward the Chesapeake Bay Bridge. Just when you think things can't get much better, First Mate, Susan Rosepepe pours you a little more champagne and brings out her homemade Anitpasto platter. A gal…

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