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

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...

August 12, 2025

X2599KKrobertam

A thrilling sailing experience!

This was our second sailing adventure with Schooner Woodwind, having had a wonderful experience three years ago. We chose the 2 hour sunset cruise this time, and it was beautiful, watching the golden...

August 12, 2025

Pavan P

Excellent overall!

Easy check in. Friendly crew and the historian was great. We were choosing between a private tour and schooner and I think we did the right thing by choosing Schooner.

TripAdvisor Traveller Rating

based on 435 Reviews

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