2-Hour Public Sailing Cruises

Our two beautiful, wooden 74-foot schooners, Woodwind and Woodwind II, offer and unparalleled sailing experience in Annapolis, Maryland.
Schooner Woodwind, Annapolis Maryland Customer Testimonials Customer Reviews

“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 Marriott Waterfront Hotel.

Each trip is unique. All cruises sail by the United States Naval Academy and then into the Chesapeake Bay. Our sailing course depends on wind speed, direction and weather. When the wind conditions are spectacular we might make it to the  Chesapeake Bay Bridge or Thomas Point Lighthouse. The breathtaking sunsets over the historic Annapolis skyline are fabulous, too.

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.

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 part of the 20th century. Her handsome mahogany brightwork, gleaming chrome and roomy cockpit distinguish her from cargo carrying work vessels.

Tickets go on sale six days prior to the date that you want to sail.

Have a group of 18 passengers or more?

If you can get a group of 18 guests or more, then you can get your tickets much further in advance. Normally, our tickets go on sale six days prior to the date that you want to sail, unless you have a group of 18 or more. We also package the gratuity into the price, so there are no extra costs.  Click here to learn about our group sailing packages or click here to download our Group Sail Brochure.

 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

History-oriented guided tour from the water on Mondays

Beer Tastings

Sample 3 different local and regional craft beers

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

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