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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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

September 10, 2026

lectrongrl

Perfect day on the water!

Perfect day for a sail! Lots of wind, splashes, laughter and peace on the water. Staff is attentive and ready to let guests participate in the sailing experience!

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...