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. Help hoist the sails (all 4 of them) or take a turn at the wheel. Our cash bar is stocked with wine and beer, including a nice selection of local micro-brews.
Sunset Sails & Entertainment
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. Our popular sunset sails start in May. Weekday sunset sails include the following events or entertainment:
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Mondays
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Tuesdays
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Wednesdays
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Thursdays
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Historic Mondays Historic oriented guided tour from the water on Mondays |
Beer Tastings Sample 3 different local and regional microbrews |
Race Woodwind vs. Woodwind II We start just after AYC series with over 100 boats! |
Local Musicians Night! Enjoy Chesapeake Bay inspired music Calendar of musicians |
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Tickets go on sale six days in advance
Rates & Schedule |
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Learn more about our Entertainment Schedule
for Weekday Sunset Sails below:
History Mondays:
Learn about the History of Annapolis and the Chesapeake Bay. The Historic Annapolis Foundation sponsors History Mondays. They have a speaker aboard educating us on different topics of the area. View Schedule
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. View Schedule
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. View Schedule
Thursday Local Music Series:
Sit back and relax as different local musicians entertain you while sailing on the Chesapeake Bay. The Singer/Songwriter genre will be well represented as they play acoustically aboard the Woodwind. View Schedule
One of the beautiful scenic views you’ll see from aboard the Schooner Woodwind
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.
