I have done that trip (at least from Oriental, NC and passing by Crisfield) almost a dozen times. How fast are you planning to cruise? Here is an itinerary if you cruise at 7 kts:
New Bern to Belhavn area- Lots of marinas. Dowry Creek is most popular. Or anchor at beginning of Alligator Pungo Canal.
Belhavn to Coinjock or Elizabeth City to do the Dismal Swamp. I like the Dismal Swamp route and the free docks at Belhavn are welcoming.
Elizabeth City or Coinjock to Portsmouth. Time your passage through the DS locks (check Active Captain for schedule) as well as the Gilmerton Bridge openings. There is an anchorage off of Hospital Point as well as free side ties at one of two pocket harbors in Portsmouth. Lots of marinas as well.
Portsmouth to Crisfield. A rather long leg at 75 NM, but doable at 7 kts. Other stops will take you quite a bit off track.
There are lots of other nice stops and side trips along the way: Oriental, Bath/Washington, Edenton, Deltaville, Reedville.
So you can do it in four days if the weather holds, but a week would let you make some of these additional stops.
David