Annapolis Sailing Cruises: Schooner Woodwind

80 Compromise St, Annapolis, MD 21401 Get Directions 
Phone: 410-263-7837

Anne Arundel

Central Maryland
Dual sailing
Field trip
sunset sailing
Schooner trip
Daytime tour
Two, 74ft schooners offer a real Chesapeake Bay sailing experience for public sails and private events. Buy a ticket or privately charter the entire boat. Raise the sails, steer the boat or just sit back and enjoy with a cold beverage.
Apr. 15-Oct. 31: Daily, 10am-6:30pm.
Maryland Green Travel Partner
Admission/Tickets Required
Green Property



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TripAdvisor Reviews
TripAdvisor Traveler Rating Based on 298 reviews
TripAdvisor Reviews
October 24, 2019
Chris P
I just completed a cruise on the Windward with Captain John and crew. I have been a sailor for over 30 years and love the water. While some “tourist” trips are a little boring with the boat motoring...
TripAdvisor Reviews
October 9, 2019
We loved our sailing trip. The trip was well organized and staff were very pleasant. I would recommend it.
TripAdvisor Reviews
September 22, 2019
I found the sunset cruise a little boring. There wasn’t much to take a picture other than the schooner and the sunset, although the sunset was great on the water. You just go straight out and...