Warm Weather Sailor
I've done the bay at night from the C&D to Norfolk. Actually it wasn't all night, there was a day in there somewhere. Not a problem, as Cam said stay near the big ships channel, especially near the bottom end where there were fish traps way out into the bay. Also a lot of unlighted buoys and range targets near Norfolk if you stray out of the main channel too far. Going into Norfolk at night to the Hospital anchorage was a bit confusing due to all the lights but not too difficult. As for the ICW 50 miles a day is a good target and doable even in winter. You have to start at first light. I hope you have a full enclosure.