Annapolis. I lived there for 35+ years. Oriental is great. Just like David says. It's a great cruising ground. Within 5 hrs on a sailboat you have: the outer banks, the Atlantic Ocean and the fantastic Cape Lookout (one of the best anchorages on the east coast), Okracoke Island, hundreds of nice anchorages on the creeks and rivers off Pamlico Sound and the Neuse River, the ICW is within 2 miles, New Bern, Little Washington, Beaufort, Morehead City, and much more. The best part is the people. At the heart of Oriental is a boating town with a little fishing thrown in. We introduced some cruising friends of ours to Oriental a couple of years ago, and they're closing on a house there at the end of the month.
We cruise to the Bahamas in the winter, where we are right now. We left Oriental 10/28 and checked into Nassau on 11/20. And that's with a 4 day stay in Charleston and 5 days in Vero Beach. By the way, Charleston is a 5 hr drive from Oriental, DC is 6. Great location!