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.


See website for hours.


80 Compromise St
Annapolis, MD
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Local Phone:
  • 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 2 by natalietro

June 03, 2021


Not worth the money AT ALL

Not much for the $70+ dollar 2 hour trip. If this was 40 a person, MAYBE, this would be better suited for what you get My family spent over $500 for this trip, and it was literally a circle in the...

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Rated 5 by Spicegirl27

May 22, 2021


Beautiful Sail on Chesapeake Bay

The perfect weather and Captain Andy and his crew made for a beautiful sail on Chesapeake Bay. We went on the 4 PM sail and it was just perfect.

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Rated 5 by Stephanie B

May 19, 2021

Stephanie B

Baby, bay, bay bay!

What a beautiful day for a sail! Even if it had been cold and dreary, we still would have had a great time. I can't say enough about how friendly and helpful the crew was. We were fortunate that the...

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TripAdvisor Traveller Rating

Rated  based on 310 reviews
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