We just completed that trip. My wife and I opted to go offshore
from Charleston to More Head
City and it took us 34 hours.
After that it was one day to South River near Oriental,
next day to anchorage Belhaven,
next day to Alligator Marina at $1 per foot -great place,
next day Elizabeth City for a free dock
next day to the Dismal Swamp visitor center free dock
next day Hampton River anchorage
next day south side of Deltaville anchorage
next day Soloman Island anchorage
next day Rhoad River anchorage which is just south of Annapolis which we could have made.
We did run into weather
and spent about 5 days, I think, holed up waiting for it to improve.
We both felt that the offshore
leg was the easiest. We picked a very benign weather
window and ended up motoring for 2/3 of the way but it was still much easier than the ICW since we made one course change when we rounded Frying Pan Shoales. The rest of the time we counted dolphin visits and sea turtles.
Hope this helps,