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 mrdesign

November 01, 2022


A Great Day on the water with an exceptional crew in a lovely ship.

Strongly recommend as a must do for all locals in the Annapolis/DC/Virginia areas, do this for a fun-great experience ,not only to entertain out of town guests. My family of three sailed in late...

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Rated 5 by Jerijoe

October 18, 2022


Boat Show excursion

Perfect sailing day, the crew was exceptional. Everyone involved in the booking and sailing was totally professional.

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Rated 5 by Sarah L

October 01, 2022

Sarah L

Must do

The sailing cruise was the highlight of our trip to Annapolis. The crew is very knowledgeable and entertaining.

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TripAdvisor Traveller Rating

Rated  based on 349 reviews
based on 349 Reviews
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