Archis...how big is the boat? For reference....
day1...Oriental to Bellhaven
day2...Bellhaven to Alligator River Marina/or anchorage
day4...to Norfolk (requires early start to clear bridges)
day5...to Deltaville or Reedville VA depending on progress
As an alternative...once you hit Norfolk, you could head up the Bay round the clock without stopping, taking turns keeping watch and be in Baltimore in 24 hours....making it a 5-6 day trip with weather cooperating.
At least the stops above will give you some idea of what some good places to exchange duties with a hired captain would be.