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

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 24, 2025

anonymous4047

Wonderful sail!

We had such a lovely morning sail! Both my new husband and I have sailed in the past but it’s been a long time. The quiet and beauty of the bay was amazing! The crew was very friendly and informative.

September 22, 2025

mikehB6633BP

Great trip

Great sailing experience. Friendly informative crew and full sails. Couldn’t be better. Highly recommend, particularly for adults kids might be a little bored but a good time!

September 21, 2025

Ann A

Worth It!

Fun and pretty sunset views. Several passengers got a chance to steer. Crew is friendly and helpful. Be sure to bring a jacket just in case the wind adds a chill.