I love this area. I would love to hear how you trailer sail this area. I stopped by Whittaker Point the last time I was near Oriental looking at boats. I ended up buying a 260 for trailer sailing and I'm still working on the details of leaving the truck and trailer for a few days and the best places to do it.
Here are some shots of Whittaker and a write-up of the adventure we had there. We went and did it again in 2014. They have a courtasy van... so you launch at the city ramp, sail back, take the courtasy van to go get your launch vehicle and thats it.... easy peasy...
I also attached a write-up of another nearby trip.
In addition to those sites mentioned in the writeup.... I've sailed out of Elizabeth City many times. My recommendation would be to head southwest to Columbia NC. They have free 48 hour tie-off at the city dock and a free public bath-house. There is also a cultural center and a few neat places to explore. Go into town at the end of the day and get a burger.... see some stuff, then get a nice shower... mosy down the river a bit and tie off in the salt marsh for the night. Usually there is a nice breeze to keep you cool at night. The next day you have to decide if you want to go to Edenton or Aligator Creek. Edenton is a fun town and also has free 48 hour amenities.... Aligator Creek has a bath house and a place to buy a burger but there is not touristy things to do there. And the mosquitos are bad.... But if you are heading to Nags Head or Roanoke Island, that is the place to hold over for the night.