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From May 11 until August 25, the graceful 74-foot schooners, Woodwind and Woodwind II, will sail the Chesapeake Bay four times every day on two-hour tours. Romantic couples should come aboard for the final trip of the day, the romantic Sunset Sail.

Annapolis calls itself “America’s Sailing Capital”, and these magnificent yachts will give you the most scenic vistas of Maryland’s beautiful and historic capital. TripAdvisor gave the Woodwinds their Certificate of Excellence in 2016.

Woodwind and Woodwind II

Designed to sail the Chesapeake Bay, Woodwind and Woodwind II, feature two masts, gorgeous mahogany brightwork, sparkling chrome, and comfortable cockpits. Intended to be nostalgic, the Woodwinds call to mind the classic, speedy schooners that were deemed “yachts” at the beginning of the 20th century.

Public Sailing Cruise Sights

The 2-hour Public Sailing Cruise delivers breathtaking vantage points of the Annapolis Harbor, United States Naval Academy, Severn River, Chesapeake Bay, and the Annapolis skyline. Depending on wind direction and speed, the cruise will be able to sail close to the Chesapeake Bay Bridge, Thomas Point Shoal Lighthouse, and Kent Island Regattas.

Sunset Sail Theme Days

The Sunset Sails on weekdays offer the following themes and events from Monday to Thursday:

• History Mondays

• Beer Tasting Tuesdays

• Wednesday Night Races

• Thursday Local Music Series

Fridays, Saturdays, and Sundays do not provide entertainment, but stunning views of Annapolis, as well as its spectacular sunset, will thrill passengers.

For More Information: Schooner Woodwind Sunset Sails

Your Inn Near the Woodwinds

The Annapolis Marriott Waterfront Hotel, where you will come aboard, is less than half a mile away from Gibson’s Lodgings, a historic inn located in downtown Annapolis offering superb accommodations and free parking for guests.

Gibson’s three houses host 20 fully-furnished guest rooms, with three 19th-century parlors, a dining room, conference room, and a beautiful central courtyard. See the photos of our beautiful rooms by clicking on the link for each house below.

Berman House

Lauer House

Patterson House

Call us to reserve your room at our toll free number (877) 330-0057. We’ll be very happy to serve you and your family throughout the year.

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