Sunset Sails

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

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.

Let our captain and crew make your trip most enjoyable and memorable.  Our cash bar is stocked with wine and beer, including a nice selection of local, independent craft beers.

Tickets go on Sale 6 Days In Advance, Buy Tickets Now


Due to current COVID-19 restrictions, our weekday sunset sail entertainment has been put on hold. We look forward to offering History Mondays, Beer Tasting Tuesdays, Racing on Wednesday Nights, and our Thursday Local Music Series when the State of Maryland says it is safe to do so.

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