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Or is stepping within the bounds of the city enough? Assuming I walk into a city for the first time and immediately try to use fly, would it fly me directly to the Pokemon Center despite me never having been there, thus saving me the effort of having to search?

Thanks in advance,
Rex

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You mean USUM/SM? I think you can only fly on places you have visited. The exact place, but I'm not sure.

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Generally, simply entering a flyable location is all that is required to be able to use Fly for that location. There are some exceptions, however, such as Opelucid City in Black and White where the player must first view the Team Plasma event, Lacunosa Town in Black 2 and White 2 where the player must first encounter Professor Juniper and Bianca, and Ever Grande City in Ruby, Sapphire, and Emerald where the player must first climb the waterfall. The Johto Battle Frontier, by contrast, can automatically be accessed after the National Pokédex is obtained.

No, most of the time, you do not have to have visited a Pokemon Center in an area that you can fly to in order to fly to it.

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Since you said most of the time, what are the exceptions?
tysm, fren (:
@Espeonage
Actually read the answer before you ask questions about it.
@Hellfire  
Nice job, you edited the question as a defense for yourself.
Once again, actually check things before you say something about it. I didn't edit anything.
It was covered up by the BA. Since this is a very stupid argument started by my stupidity, let's end it here.
Actually HT is rigth. he didi not edit anything