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You won't be doing much sailing in the ICW. Count on motoring about 8hrs/day. There are few outside jumps to consider - Beufort to Mayboro, Caoe fear to Charleston, Hilton Head to St. Simon' Island, St Simon's to Fernadina, Fernadina to St. Augustine. These are all close to coast Jumps and should be made with one overnight. The run up Delaware Bay to the C&D canal can be a bear but it gets you into the Chesapeake. It would be about 150 miles to Norfolk but thjere are lots of stops on the Bay. The other course is to run the DelMarVa peninsula withfew palces to stop. You should plan on being in the Chesapeake befor November.