2 Hour Public Sailing Cruises

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

Due to COVID-19, we have delayed the opening day of our season,  At this time we are unsure of our start date but will update here as soon as we know.

“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:

Guided Historic Sailing Tours on the Chesapeake Bay

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.

Public Sailboat Racing America's Cup Style in Annapolis Maryland

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.

Annapolis Public Sunset Boat Ride

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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