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. 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.

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 part of this century. 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.


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.


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

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