I don't think you will find anything like that ...
I used to make regular spring and fall windsurfing trips to the OB's and many family vacations to Nags Head & other locations in the summer. We never saw ANY sailboats of any size in those areas. I used to trailer our Hobie 16 and sail it in Roanoke Sound from Nags Head to Kitty Hawk. The problem is that the water is way too shallow for vast areas of water inside the Outer Banks and there is virtually no access to the ocean for a sailboat. Oregon Inlet has nasty currents and ever-changing shoals. The marinas on Roanoke Island are virtually all filled with sport fishermen. You may want to look in Manteo on Roanoke Island for the only possibility. I never even noticed any marinas along the stretch from Kitty Hawk to Nags Head, probably because the water is too shallow to get in anywhere. Obviously there is nothing on the outside, except vast stretches of ocean front beaches. You can rent windsurfing gear or kite sailing gear (or take lessons) at Kitty Hawk Sports in the complex right across from the sand dunes (if they are still there). I think they also have facilities in Nags Head. Look for the sound-side facilities as you are travelling south just before you get to the intersection that takes you to Roanoke Island. All windsurfing and kite sailing in that area is on the sound. To use the ocean for windsurfing, everybody goes south to Cape Hatteras. In the later summer, especially August, there will only be wind if a front is passing through. It can blow very strong for a few days (if you are lucky enough to catch a front) and then be virtually still for days on end. There doesn't seem to be any in-between gentle winds. The Hobie Cat wasn't much good most of the time in the summer because the air is too lifeless. The spring and the fall is when the fronts move thru far more often. It seems to me that along that area of the coastline it is either blowing 30+ or not at all ... in the summer 95% not at all. I suspect that is why I have never seen a sailboat in the whole stretch of water from Kitty Hawk down to Cape Hatteras either soundside or in the ocean.
