Mostly traveled the U.S. I'm going to do this skatewise, only including places I've skated.
Chicago- Grew up there, one of the most Amazing cities in the world
Milwaukee- visited while I lived in Chi, some good shit downtown, a good place to skate another city if you live in/near Chi
Madison- same idea as Milwaukee, but with college kids
Cincinnati- some dope shit, skated the dyrdek plaza nearby. Figured out why all the new skate plazas have metal edges on the ledges
Philadelphia- Love, city hall, all that shit were going off first time I went, now its not about that but I stand by the fact that there are still plenty of cool cutty spots there. Also, FDR kills it
NYC- fuck yeah. All that can be said
DC- Hot and muggy, historical shit everywhere, skated pulaski and some random shit around the city
Miami- just skated some shit by the hotel my family was at, Miami seemed cool when I was 16
St. Louis- St. Louis is actually pretty sick. They got a DIY park going and a lot of good cutty spots
Santa Cruz- very little to skate there for a city that serves as headquarters for santa cruz, creature, consolidated, indy, and ricta. Still an amazing place. The new park is fun as fuck. Secret about derby park: not that fun, still gets love because it is a classic park
San Jose- Know somebody or you'll miss half the spots. Lame culture, cool spots.
San Francisco- HILLLLSSSSS. I'm pretty sure this place is heaven on earth, skatewise, culturally, it just doesn't get better than this town
Oakland- SF's low key neighbor. I lived here for a while. Its become quite the DIY mecca in its own rite. Dope town.
LA- spots everywhere. So much good shit to skate, a lot of it is just pretty spread out. Definitely worth visiting, but I wouldn't want to live here, too bad I do.
San Diego- Man, FUCK San Diego. Washington street is fun, but really, overall its pretty blown out, and a lot of the bad shit you hear about LA is more true in SD (its spread out, you gotta know where spots are, there is no downtown, people are made of plastic...)
Sacramento- Probably need somebody to take you around (I did), but it has some cool spots for sure. I still hold a slight grudge against it after I broke my foot trying to ollie the triple set
I can't think of any other U.S. cities off the top of my head, so lets go international now (much shorter list)
Ensenada, Mexico. I hear its all drug warred out now, but back in the day it wasn't, and there is a lot of really cool and unique shit to skate there. Right outside of town we took a road to a place call la bufadora to camp, on the way we found 5 empty pools right by the road. 3 were skatable. Fuck yeah Ensenada. Too bad they probably stash bodies in those pools now.
Vancouver, Canada- I went when I was 17, which was 11 years ago. Back then, Vancouver was still pretty much the Canadian SF. Skated that one spot they skated in the Plan B videos with all the ledges and the two sets of stairs, I think it's called the new spot. So much other good street skating to be had. I hear it's not quite like that these days though. Bummer.
Brussels, Belgium- I was 13 and was hyped to frontside 180 a 3 stair, so I don't know if I can give a good review. They do have a good 3 stair apparently though.
Paris, France- pretty awesome. Skated by the eiffel tower at that plaza with all the stairs and banks next to them (Soy Panday skates in static 3 I believe) Paris is a pretty cool city overall
London, England- South bank was dope. England weirds me out though. No particular reason why
This summer I'm on my way to Peru
I've wanted to go to Barcelona for a while, but everytime trip time comes up I back off and think its uncreative, but I'm over it, Barcelona looks sick and I need to go. Maybe on a trip through the mediteranean region.