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Climb Aboard the Schooner Woodwind for a Sightseeing Cruise

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Schooner Woodwind Annapolis Sailing Cruises take guests out on the open waters of the Chesapeake Bay for a couple of hours of sightseeing, food and drink, or even a live concert. In the warm summer months, the pair of 74-foot wooden schooners— the Woodwind and the Woodwind II—ferry sightseers past the U.S. Naval Academy, the Annapolis Skyline, and the mouth of the Severn River, as well as other local landmarks.

Snag a ticket to a public day or sunset cruise or book a private charter if you have a group of 18 people or more. The schooners also play host to specialty cruises throughout the summer and early fall, like the upcoming Wine in the Wind cruises on July 15th and August 12th, which feature tastings of top-shelf wines. Keep an eye out for dinner cruises and brunch cruises, too, which include a full meal.

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