Woodwind sails up to four times daily from the Annapolis Waterfront Hotel. Each trip is unique. All cruises sail by the United States Naval Academy, into the Severn River and then into the Chesapeake Bay. Check out the fun sunset sails that we have lined up this year.
Sail away and raise your glass on a “Wine in the Wind” cruise, learn about Lighthouses on the Bay, indulge on a dinner cruise featuring local food, or sit back and relax and enjoy the fireworks on July 4th. Or maybe you want to celebrate Mother’s Day or Father’s Day with a delicious brunch? Check out our calendar of events.
Every October, we sail on two, multi-day cruises on the scenic Chesapeake. One is an exciting race down the length of the Bay (130 miles). The other is a 5-Day adventure cruise 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.