“My husband and I sailed with you on last Saturday evening’s sunset cruise…we were with our dear friends who were celebrating their 25th anniversary. We all had such a wonderful time! Candidly, I was a bit apprehensive, having never sailed before and not knowing what to expect, but I will definitely be back! We all will. Thanks again, so much, for a wonderful adventure.”
Marieanne H.
“We love sailing on the Woodwind and Woodwind II; It is part of our summer plans every year, especially when family comes from out of town. The crew is always fun and professional and each sailing is a new adventure!”
The Paulsons
Urbana, Maryland
“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 most enjoyable and memorable. Help hoist the sails (all 4 of them) or take a turn at the wheel.
All of our cruises will see:
- United States Naval Academy
- Annapolis Harbor
- Chesapeake Bay
- Scenic views of Annapolis skyline
- Severn River
Depending on the wind direction and speed, you may see:
- Chesapeake Bay Bridge (we may even go underneath)
- Thomas Point Lighthouse
- Kent Island
- Regattas competing in the Bay
- Ospreys and other local birds
- Watermen checking their catch
The 74-foot schooner “Woodwind” and “Woodwind II” were custom designed and built specifically for sailing on the Chesapeake Bay. Woodwind is a replica of the classic, fast wooden schooners that were built as “yachts” in the early 1900’s. Her handsome mahogany brightwork, gleaming chrome and roomy cockpit distinguish her from cargo carrying work vessels. Our cash bar is stocked with wine and beer, including a nice selection of local micro-brews. Click here to download our Public Sailing Brochure
Have a group of 18 passengers or more?
You can get your tickets further in advance and pay the gratuity up front. Click here to learn about our group sailing packages or click here to download our Group Sail Brochure.
Weekday sunset sails include the following events or entertainment:
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.
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.
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.
