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Sailors based on the Chesapeake and Delaware bays have used a round the DelMarVa trip as cruising goal for many decades. Thad Van Gilder, the Chesapeake Bay Fleet Captain, has completed this trip more than 15 times, including once onboard his unpowered 1923 Falmouth Quay punt. Safety, watches, routes, suggested anchorages and docks will be discussed. In addition, Itineraries, timelines, and an itinerary that does not involve an overnight passage will be discussed. This class has been offered for several years to a variety of sailors, and this year will be offered to members of the CDSOA.