Thanks for the input. When I said "straight through" to Cape Charles, I meant doing that leg in passage making mode, then deciding how to do the rest of the trip. Of course, if the winds don't cooperate, we could always go gunkholing - plan B - from wherever we run out of wind.
I actually have closer to 10 days than one week for the trip. The Rehoboth Bay Sailing Association has itineraries posted on their website where they've made circumnavigations of the peninsula in 11 days, doing no more than 50 miles per day and no night sailing.