I've ridden in every mainland country in the Americas--north, south, central--plus a couple of islands. The only place I've had any real difficulty was Cuba, where a very dedicated public servant spent the better part of a half-hour in the tropical sun struggling to get a complete, clear rubbing. Opportunities to ship your bike into Cuba are severely limited (and expensive), but if tempted you might want to think twice.
Hope that's helpful.
Mark
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