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 Dawn J

July 29, 2025

Dawn J

Great sailing!

Great crew and wonderful experience! Crew dealt with my grandchildren very well and were very patient and tolerant of my threenagers !

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Rated 5 by Paradise801376

July 26, 2025

Paradise801376

Excellent

As part of our travels to Annapolis; we always make time to go on the Woodwind and share our experiences with the friends we are traveling with at that time. This year we were treated to an amazing...

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Rated 5 by Kathy F

July 26, 2025

Kathy F

Sunset cruise

The boat was beautiful, the sunset was perfect and the crew was superb! We would definitely sail again with this captain and crew!

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TripAdvisor Traveller Rating

Rated  based on 431 reviews
based on 431 Reviews
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