New Orleans.
Great culture, tons of history, fantastic food and music. It is a tourist town, so you'll find many friendly folks. Sure, there's the seedy underbelly, but a lot of what you hear is overblown.
I also enjoy Washington D.C.
You could spend days in the Smithsonian museums, and most of the touristy stuff is free! Great little cities around D.C. as well, the power center of the U.S. and multitude of universities makes it a unique place to go out on the town.
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