Annapolis and the Chesapeake Bay is a mecca for individuals with a passion for things to do on the water. Our sailing schools, regattas, and weeknight races provide lovers of all things water with a daily fill of waterfront magic. A host of Annapolis public cruises, private charters, kayaking, canoeing, and paddle boarding opportunities make it easy for kids of all ages to don their water wings and make like a local.
Surrounded by the Chesapeake Bay, four rivers and more than 400 miles of shoreline, we are proud of our maritime heritage. Spend a Sunday afternoon exploring the things to do in Deale, Shady Side, and Galesville, and you’ll discover just how much the rivers and Bay have shaped the lives of generations of farmers and watermen. The pace picks up as you head toward BWI Thurgood Marshall Airport. Home of Fort Meade and the National Security Agency, Annapolis Baltimore is the cyber security capital of the nation and home to the new Maryland Live! Casino.