Public Cruises

Due to COVID-19, we have delayed the opening day of our season, At this time we are unsure of our start date but will update here as soon as we know.

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Specialty Cruise Calendar
Specialty Cruise Calendar
Sail away and raise your glass on a “Wine in the Wind” cruise, learn about Lighthouses on the Bay, indulge on a dinner cruise featuring local food, or sit...
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2 Hour Public Sailing Cruises
2-Hour Public Sailing Cruises
“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...
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Multi-Day Cruises
Multi-day Sailing Adventures!
Unforgettable 5-day, 4-night adventure cruises on the Chesapeake Bay. No experience required. Learn the basics of sailing and navigation, or just relax and enjoy the scenery.
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Sunset Sails
Sunset Sails & Entertainment
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...

Rates & Schedule

Schooner Woodwind • at the Annapolis Waterfront Hotel • 80 Compromise Street • Annapolis, MD 21401 • 410-263-7837

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