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.

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Location

80 Compromise St

Annapolis MD 21401

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Central Maryland

	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

August 27, 2026

lindalrodgers

This company is not honest. Don't support them.

This company deserves zero stars. Before you purchase the pricy tickets, read ALL the 1 star reviews. I wish we had. They will firmly tell you, "we are sailing regardless of weather". And they...

August 24, 2026

Camper50488286907

Finally took the sail after living here for decades...why did I wait so long A great uplifting experience

What a wonderful romantic time we has on a sunset cruise. Weather was perfect as was the sailing. Captain was super informative about local history. We all had a chance to steer the boat and get...

August 23, 2026

Caroline G

Overall good experience with one exception.

The sailing was enjoyable and Capt. Mickey, Ewan and Paul were friendly and attentive to everyone on the cruise. Ewan and Paul were especially helpful on the side where we were sitting. The one...

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