Mission1

Sail Annapolis on a Schooner

Schooner Woodwind in Annapolis. Sail the Chesapeake on a wooden schooner and take the wheel.

Sail out of the Annapolis waterfront on a classic wooden schooner, and pick an evening sail to catch the sunset over the bay. When the crew asks for help, volunteer: raise the sails together or take a turn at the wheel. The photo to get: the two of you at the bow with the sails full above you.

Date
1-3 hours
Easy
Over $60
Outdoors
Spring, summer, and fall
Best in the evening

Check before you go: tickets, and weather and trail conditions

Schooner Woodwind, Annapolis waterfront80 Compromise St, Annapolis, MD 21401

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Checked October 2026

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About this place

Annapolis calls itself the "Sailing Capital of the World," and from the water you'll pass the U.S. Naval Academy and see why. The Woodwind schooners are about 74 feet long, and a typical sail takes about two hours out onto the Chesapeake Bay.

Sails run from spring through fall and depend on the weather. Bring a layer, since it's cooler on the water, especially at sunset.

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