Annapolis Sailing Cruises: Schooner Woodwind

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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. Learn about sailing, the ecology of the Bay as you sit back and relax with a cold beverage. A recognized Chesapeake Bay Storyteller, trained by the Maryland Office of Tourism.
Hours See website for hours.
Location
80 Compromise St
Annapolis, MD
21401
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Contact
  • Admission/Tickets Required
  • Catering Available
  • Educational Resources Available
  • Family-Friendly
  • Green Property
  • Group Tour Rates Offered
  • Group-Friendly
  • Guided Tours/Guide Available
  • Maximum Group Participants
    80
  • Meeting Facilities
  • Student Group-Friendly
  • Tour Length
    2 hours or more
  • Video Link
    https://www.youtube.com/watch?v=WTQCReY96r8&t=10s
  • Weddings
Rated 5 by LenB898

July 14, 2025

LenB898

Bradley's at Sea

This was a perfect way to spend quality time with family out on the water. Woodwind II was beautiful and the crew was awesome. The Bradley's had a wonderful time. Highly recommend a sail on the...

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Rated 5 by Colleen P

July 13, 2025

Colleen P

Beautiful Sailing!

We loved our experience on this ship. The small numbers make it seem very intimate. The crew does a great job of explaining sailing to those of us who have no idea and have never been on a sailboat...

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Rated 5 by marybB2685ZC

July 10, 2025

marybB2685ZC

Sailing adventure

Delightful sail, wonderful vessel, excellent captain and crew, great refreshments. Kids enjoyed helping with sails and helming

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TripAdvisor Traveller Rating

Rated  based on 427 reviews
based on 427 Reviews
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