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 5 by DiAlJo

October 09, 2021


Sunday 10:00am Sailing Event

On our Trip to Annapolis = taking a Sail was one of the activities we wanted to do. We booked tickets on Saturday for a Sunday 10am sail based on the weather looking really good. We arrived early...

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Rated 5 by DJMAN5

September 27, 2021


Afternoon Sailing Adventure

After the Naval Academy, this was # 1 thing to do. We went on the afternoon cruise and were very fortunate to have a perfect sailing day- great weather & good wind end of Sept. Note - no refund for...

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Rated 5 by williamcX3668BB

July 21, 2021


A great relaxing way to see the Annapolis harbor and the Chesapeake

We were a group of 5 and had a great sail on the Woodwind. The Captain and the crew knew what they doing. They got all that wanted to take a turn at the helm the opportunity starting with the...

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TripAdvisor Traveller Rating

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