Woodwind sails up to four times daily throughout our summer season from the Annapolis Marriott Waterfront Hotel. Each trip is unique. All cruises sail by the United States Naval Academy and then into the Chesapeake Bay. Sailing under the Chesapeake Bay Bridge is a fabulous experience, as are the breathtaking sunsets over the historic Annapolis skyline on the sunset sail.
Sail away and raise your glass on a “Wine in the Wind” cruise, learn about Lighthouses on the Chesapeake, indulge on a dinner cruise featuring local food and beverages, or sit back and relax and enjoy the sunset sail and fireworks on Independence Day. Check out and buy tickets now from our calendar of events featuring these specialty cruises and more!
Every mid-October, we sail the Woodwind on multi-day cruises on the scenic Chesapeake Bay. The first is an exciting race down the length of the Chesapeake Bay (130 miles). The second cruise is a 5-Day adventure cruise back up the Bay from the Norfolk, VA area to Annapolis where we anchor (or dock) in a quaint harbor or town as we explore this fabulous region during fall foliage.