Experiences traveling with skates

I was wondering if some you guys/girls with travel with your skates and how your experience has been. Are there especially "skateworthy" cities you can recommend? Cities where skating might be limited or prohibited heavily?

After seing the video recently of people skating into the Manhattenhenge, the idea of exploring a new city with skates did stick with me somehow. That bears the problem of traveling with your gear (which might be cumbersome). Thus the question.