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.

Hours See website for hours.

Location

80 Compromise St

AnnapolisMD21401

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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 01, 2025

Riddlerindc

Sunset Tour = Perfect Way to Celebrate 21 Years!

We had an absolutely unforgettable evening aboard the Schooner Woodwind in Annapolis to celebrate my son’s 21st birthday. From the moment we stepped aboard, the crew went above and beyond to make the...

July 01, 2025

mama2carter

Great experience and super friendly crew

The crew was excellent! The two-hour sail was so pleasant and enjoyable! I would recommend it to anyone!!! Thanks for making it a memorable ride!

June 22, 2025

jamakem

Best Sail Ever!

Recognizing that Captain Jen, Jacob, and Joey cannot have had much control over the weather, it could not have been a nicer sail! Perfect weather, perfect crew, perfect companions! We're confirmed...

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