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 bar is stocked with wine and beer, including a nice selection of local, independent craft beers available for purchase aboard.

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


Guided Historic Sailing Tours on the Chesapeake Bay

History Mondays

A guided tour exploring the history of the area, the Chesapeake, and the sights you see while on a sail. Each week we will focus on a specific interesting topic with a guest speaker aboard. Early May – September.


Beer Tasting Tuesdays

Sample while you sail! Each month we feature a different brewery from the Mid-Atlantic Region, and their representative comes aboard and teaches you about beer. 3 samples of beer come with the cruise, and then order full beers from the brews that you enjoyed the most.  Schedule of Breweries.

Wednesday Night Races

Join the crew and race Woodwind vs. Woodwind II every Wednesday night from April 25 through August 29. 130 other sailboats are also racing in the Wednesday Night Regatta. Wednesday’s are the nights to Party Like A Sailor.

Annapolis Public Sunset Boat Ride

Thursday, Friday, Saturday, and Sunday

There is no “specific” entertainment on these days of the week. There is so much to see as we sail by the United States Naval Academy and into the Chesapeake Bay. Let the crew grab your favorite beverage as you relax watching the sun set over the city skyline.

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