Sunset Sails

Sunset Sailing in Annapolis Maryland on the Schooner Woodwind

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:

Guided Historic Sailing Tours on the Chesapeake Bay Tuesday Night Beer Tasting Public Sailing Cruises Wednesday Night Public Schooner Racing Thursday Night Music Sunset Sails

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
Tickets go on sale six days in advance
Rates & Schedule
Schooner Woodwind Weekend Sunset Sailing Cruises in Annapolis, MD

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

Scenic views of the Chesapeake Bay

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.

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