2 Hour Public Sailing Cruises

Daily Public Sailing

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“Woodwind” sails up to four times daily throughout our summer season from the Annapolis Waterfront Hotel. Each trip is unique. Let our captains and crew make your trip most enjoyable and memorable. Help hoist the sails (all 4 of them) or take a turn at the wheel.

Special Events Calendar

Special Events On Sale Now

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Throughout the sailing season, we offer special events that make any day exceptional. Embark on an unforgettable tour with a carefully crafted menu of food and drink. From special Mother’s & Father’s Day cruises to lighthouse cruises, seeing the Blue Angels overhead, and many other special occasions.

Sunset Sails

Sunset Sails & Entertainment

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Sunset is a favorite time for a sail on the Woodwinds. The sunset over the Annapolis skyline is breathtaking. The golden glow reflecting off the sails as the sun descends near the horizon is an unforgettable sight.

Group Sailing

Why book a Group Sail?

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Group Sails can purchase tickets further in advance. Public Tickets can only be purchased six days prior to the date you want to sail. All Service Fees are included on Group Sails. Guarantee the sail will not be booked for a private event.

Great Chesapeake Bay Schooner Race

Reserve your spot early!

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Participate in a breathtaking Parade of Schooners racing 130 miles from Baltimore’s Inner Harbor down the Chesapeake to Thimble Shoal at the mouth of the Chesapeake Bay.