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 JillyinMI

July 03, 2022


What a great way to end a day of touring Annapolis!

We had a beautiful night for a sunset sail! Captain Jen and her crew made the excursion so fun and memorable. If you are in Annapolis and are looking for a unique experience, definitely book a...

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Rated 5 by mcleapyear

June 17, 2022


Really fun!

We are "return Schooners"! We took a sunset cruise year 3 years ago and loved it so we tried the 4 - 6 PM trip. Capt. Mickey was terrific! Knowledgeable, personable and it was clear he was an...

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Rated 5 by 180susanms

June 16, 2022


Schooner Soon! A Sailing Delight

The weather was very cooperative and the cruise was awesome. Capt. Mickey and his crew - Allison, Sophia & Stephanie - were very personable and knowledgeable about the local area and the boat. They...

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TripAdvisor Traveller Rating

Rated  based on 328 reviews
based on 328 Reviews
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