Okay, the plan is something like this.

Take a city map (nice street-map type map) from a city.
Invent a suitable apocalypse (I will avoid the Zombie-pocalypse options).
Draw all over the map to detail the changes to the city, in its post-non-Zombiealypse state, also random notes, etc.
Weather it.
Distress it.
Make it look like it is owned by a post-apocalyptic hobo.

Now... which city...

Japan (cliched but suitable for any large dinosaur-monster type apocalypse)
Shanghai (nice city, been there and walked over a lot of the downtown district, great train system)
Sydney (Domum dolce domum)
Melbourne (just because I can...)

Any other cities people think should be destroyed by an apocalypse? I'm kind of willing to take requests here...