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The Bay is certainly doable at night, but why rush? You are leaving the best cruising grounds in the the US so take a deep breath and enjoy the ride. I would say the trip is at least 3 days (summer time) and maybe 4 if weather gets in your way. I have sailed pretty hard from West River to Mobjack Bay (just north of the York River in 2 good days) and HG is at least another day from here. I have never done the ICW south but have considered it. Those seem like long days too with too much motoring and too little sailing.
