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

July 05, 2026

Flyer38423137649

Great Experience

Great Experience Fantastic crew Very informative too about Annapolis history ..

July 04, 2026

Shellita1

Captain Andy makes this trip enjoyable!

Captain Andy and his crew explained the steps to hoisting & control of the sails, understanding wind direction, history of the boat, site's along the shore,etc..it was very educational and...

July 02, 2026

packyourbags123

Wonderful 2 hour dail‼️

Our experience was great/ much more than I expected! With most trips like this the boat moto-sails. But yesterday, a perfect day for sailing, all sails were raised. We had a wonderful 2 hour sail...

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