When Does a Destination Become a Caricature?

When has a developing country’s historic town passed the point of pretty gentrification and become, well, “spoiled”?

When local real estate prices make your home city seem like a bargain?

When there’s a jewelry store on every block?

When the tourists and expats outnumber the locals in the center of town?

When there’s a “Berlin Bar” on one side of the street and a “Dublin Pub” right across from it?

When you can throw a baseball from the city’s best-known monument and hit a Starbucks sign?

When none of the people working in the middle of town can afford to eat at any nearby restaurant?

Or is it when two guys are working on their laptops on a park bench—in the Plaza Principal—in Mexico?

When Does a Destination Become a Caricature?

I can think of a few places in Mexico that hit a few of these points, like Playa del Carmen or central Puerto Vallarta. But I’ve just spent a few days in a town that is “all of the above.” If the thought of that makes you shiver, then you will probably not want to put San Miguel de Allende on your must-visit list.

Yes, it’s an undeniably beautiful place, with pretty street signs on movie-set-perfect cobblestoned streets. Almost none of the buildings need a paint job. The largest city park is cleanest one I’ve ever seen in Latin America. You can find pretty much any kind of food you want and the upscale inns are oozing with enough aesthetic charm to make the most jaded interior designer giddy. Even a reluctant shopper like me could spend a fortune in this town and come away with stuff I would love forever.

But jeez, the place feels kind of creepy. Something is off, like it’s been perfectly presented to meet the needs of 60-something travelers looking for just a tinge of the exotic among the familiar. (The main hair color here among the foreigners is gray. #2 would be “dye-job.”)

San Miguel de Allende is a photographer’s dream, but I feel sorta like I did when I was in the Nepal or Africa sections of Disney World . A stylized version of the real thing, with all the messy parts removed. If you’re here and you see some character disappear into an underground tunnel and then see an identical character come out to take his place for photos, then if I were you I would run for the hills…

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