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

August 25, 2025

Kym B

beautiful sunset cruise

Relaxing sail of the Chesapeake Bay with a trusted crew on a beautiful boat...what could be more relaxing & restorative than catching a sunset cruise.

August 21, 2025

Beverly D

Woodwind Sailing Fun Evening Out

Excellent experience. Captain was experienced, crew way friendly. We have done this several times, and have always loved it. Each time is different depending on weather, wind, what night of the...

August 13, 2025

Joshua S

Amazing and relaxing

Here’s a short, attention-grabbing version for the TripAdvisor review list: ⸻ Amazing trip—so good I went twice! Fun, knowledgeable crew, stunning ocean views, and even got to steer the ship and...