Annapolis Sailing Cruises: Schooner Woodwind

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.
80 Compromise St
Annapolis, MD
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  • 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
  • Meeting Facilities
  • Student Group-Friendly
  • Video Link
Rated 5 by Tiffany C

November 28, 2023

Tiffany C

Always such an incredible time!

Such an incredible time! So beautiful and peaceful! The staff is amazing. I have been going for years and EVERYTIME it has been wonderful!

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Rated 5 by Michael H

October 16, 2023

Michael H

Memorable day on the water

Excellent experience and fantastic crew! Joined for 90 minute cruise out into the Chesapeake during the Sailboat Show and was great! Crew was great creating awesome memories and photos for the kids...

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Rated 5 by linda m

October 01, 2023

linda m

Best sail in Annapolis

Second time on sunset cruise. A must do if visiting Annapolis. Lovely views, great crew, special photos with friends. We plan to sail every time we visit Annapolis and east to book online.

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TripAdvisor Traveller Rating

Rated  based on 385 reviews
based on 385 Reviews
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