Hi Nial, I've singlehanded this both directions, also agree that the Chesapeake is about as good as it gets for this situation. You can get down the bay in 4-5 days taking it a little bit easy. In the event of a weather
shift and a fresh N wind, you can hop on that and ride. I had a killer trip back down the bay last summer running overnight in 25-30 knot
winds. Took me a day to cover what took 3 days of hard motoring coming N.
Definitely slow down and enjoy the ride, the Chesapeake is a great sailing destination
and you can tack back and forth across the bay to your anchorage. For me it is way more fun if each nights anchorage is my destination
and I can enjoy the adventure without feeling like every day is a sacrifice to get where I really want.
Of course NC is home, and boy do I love it down here. Once you have cleared the Dismal (it's just a better route for singlehanders in small boats imho) you can sail down the PAsquotank in prevailing SW (which has been blowing 20 steady with gusts to 25 here lately) to the Albemarle. Little River is a good anchorage just west of where you spill out to Albemarle. At that point you can sail the Pamlico Sound down to the Neuse, either via Manteo and Ocracoke
, or down western PAmlico via Croatan Sound. There is a bridge there with 45' clearance, so that's a great route if you want to make tracks south.
The crab pots can get thick in the Albemarle - beware. I crossed Albemarle in 20-25 knots last summer motor
sailing, could not point high enough. I wrapped a pot and then watched my stern rise and fall about 5' -very lively- and dreaded getting it cleared. I restarted engine
and bumped it in reverse a couple of times and got lucky, but contingency was to limp back down wind under sail to sheltered waters and clear it. I think it should be mandated that they use bright colors, the black colored floats are a joke as far as visibility.
Have a great trip on your sweet boat-