1. New York and New Jersey. My birthplace, and where I grew up, respectively.
2. London. In Europe (which I haven't seen nearly enough of) and said to be culturally rather like New York.
3. Tokyo, very big city, bound to be pretty interesting.
4. Los Angeles. Large city, sunny part of the world, brand-new rail system worth studying, in California.
5. San Francisco. (Of course.)
6. Washington, DC, lots of museums, very nice.
7. Hong Kong. One of the world's densest cities with a high income, so an exciting skyline and close to many services.
8. Berlin, Germany. It was a divided city for several decades, so looking at how its division and reunification affected the city would be nice to do.
9. Honolulu, on account of having always been partial to Hawaii, since I was a kid. Only problem is, Hawaii doesn't have too many railroads.
10. Amsterdam. Sexy, associated with Anne Frank, and bicycle friendly.
If one throws language and nationality into the mix, California rises up past the European cities, Hong Kong, and Tokyo, and so does Washington, DC, although language is a reason why London's up there (although a relatively small reason). Most of the areas are dense and transit friendly; I might make an exception for Honolulu (which is dense enough and hasn't really gotten a good transit culture together, I don't think) and LA (ditto, kinda), but I generally like transit-friendly places (well, when I'm not driving, anyhow). There are also various New Jerseyan places out there, too...
If one also includes ethnicity, then, yeah, Jerusalem and Tel-Aviv would be invited into this crowd (and Hong Kong and Tokyo would suffer some demotion in the ranks as being a tad "gaijin", admittedly, although they'd still be places I'd like to visit). And there's also the temptation to head down to New Orleans to see how it's bouncing back from the hurricane.