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 07, 2025

Traveler56055645760

A great day, boat, and crew

Capt Delaney and crew, Michael and Ono provided an excellent Chesapeake Bay sailing experience. The beautiful day and wind helped make it so, but their expertise, service, and attitudes enhanced the...

September 06, 2025

lisa w

Sister birthday celebration

Went for an evening sale for my sister’s birthday. The weather was amazing the sailing was awesome. Ono with the crew was very helpful , kind, and knowledgeable. Would highly recommend this company...

September 05, 2025

Jburk77

Happy Sailing!

We had a fantastic experience for our anniversary. The office was accommodating when we were running late, the crew was fantastic, the boat was amazing and the wind was perfect. What a great day!