Top for me are Boston, Chicago, San Diego, then Miami.
I'd put New York in a class of it's own. Great place to visit.
I've heard Portland, Nashville, and Austin are great but I haven't been.
I had a work trip to Sarnia, ON once and stayed longer and went to Detroit to knock Red Wings and Tigers games off my list. I stayed downtown and it wasn't as bad as everyone said, but I also didn't wander around into the super sketchy areas. It's definitely a bizarre place.
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