I love Portland, Maine. I used to date a girl who's dad lived out there and I kept dating her longer than I should have because I loved visiting that area so much. The downtown is nice and compact, has some great restaurants, and a surprising art scene for a city its size. Wilmington, NC is another underrated place to get my vote. I used to live near there and would move back in a heartbeat if I could convince the wife. The beaches (along most of the NC coast really) are so much, cleaner, less crowded, and less expensive than what you will find in most of Georgia, SC, or Florida and the college seemed to supply a steady stream of good looking girls. My only complaint is that the housing stock, once you are right outside of downtown, is pretty bland.