Don't have any specific city. Just going to be going to Mexico, can book anywhere, but would like to head somewhere that I had a chance to sneak away and skate. Sitting on the beach gets boring pretty quick.
Two things to take into account:
1) Size of your destination: as a general rule of thumb, a city will have more to offer than a quiet beachtown. Cancun is a despicable place, but it will probably have more to skate than Todos Santos...
2) Age: Mexico has a lot of historical cities, most of which have cobblestones all over. Not so great to skate. Again, Cancun might be an example of a city with a lot of modern architecture, whereas Puerto Vallarta, while prettier, has a lot of historic buildings and streets.