I'm starting a sailing club/pirate reenactment group in Raleigh, NC and I was thinking about sailing my 22footer from Beaufort, NC to Hampton Roads for a June event.
Go up the ICW to the Neuse River and sail it down to the Pamlico...head north (sailing) till you pass Roanoke island and back into the Albemarle sound. Once out of the Albemarle it is all motoring. I would estimate total trip time at a week with daylight only sailing/motoring. Make sure you have a reliable engine as you will be motoring for at least 100 miles of the trip.
You could also trailer the boat from Beaufort to Hampton Roads, and save some time motoring. Most 22' boats are trailerables... and going 55 mph to windward beats motoring at 5 knots.
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