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
Student Group-Friendly



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TripAdvisor Traveler Rating Based on 300 reviews
TripAdvisor Reviews
June 28, 2020
Honestly I thought it would’ve been a little more exacting. The crew was nice and did a fantastic job with what they were supposed to do. They new a lot about the history. If you are looking for an...
TripAdvisor Reviews
June 16, 2020
My 20 year old daughter and I went for an afternoon sail. Things are slow right now because things are just starting to open up after the pandemic. We lucked out and got a spot last minute. Normally...
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...