Not necessarily in this order:
Portland, OR
LaFayette, LA
Whitefish, MT
Charleston, SC
Savanna, GA
Key West, FL
Butte, MT and surrounding areas
Charleston & Savanna are choked with tourists most the time but are still cool.
Portland is almost all the younger set, but has class, taste, & style that are sorely lacking in most US cities. Doesn't have a bug up it's ass like most other places.
Whitefish was super cool in the 80s. Completely laid back, kinda hicky but in a cool Montana way. It's all commercialized now with over 50% of the pop being transplants.
LaFayette, if you were ever in the thick of Cajuns with their hair down and the music blastin you know the draw.
Key West is like a non stop carnival, nudes on the beaches, a cop pulled up on me there when I was eating a meal with a qt of beer on the roof of my car behind a business that was closed for the day. He asked what I was doing and I replied, ah...ah, buh...just having my dinner. He said OK and left.
Butte is like going back in time. The people there are 100% friendly and trusting. If you go into a bar in Butte and don't know everyone in there on a personal level in the first 30 minutes there's something wrong with YOU.