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Puebla hands down, is a colonial city with a beautiful historical downtown, many interesting places to visit, with lots of history and great weather and food places.
Guadalajara represents a great image of Mexico with tequila and mariachis, a really interesting city.
Monterrey is an industrial city but has many attractions such as parks and museums worth visiting.
Guadalajara---I was just there about a month ago on a road trip. We visited several major cities in south-central Mexico, and it was my least favorite. I agree with the poster above re: Puebla. Lovely. I would also avoid Chapala (on Lake Chapala). Ajijic and the stretch leading up to Chapala were nice, but the town of Chapala was overrun by 20-somethings and they were all drunk (I kid you not!). Finding somewhere to park was a pain. Big surprise for me on this trip was Leon. We hadn't planned on going there, but somehow ended up there--and we loved it!
I've travelled extensively (and lived for two yrs) in south-central Mexico for the past 10 years. I definitely have my favorites! Happy travels.
i just got back from Puebla this past weekend. Did a weekend getaway there. Actually stayed in Cholula but spent half the time in Puebla too. I liked it a lot. It's got a cool downtown/central area. Interesting architecture, cool restaurants, interesting food. It seems to be a tranquil city overall. Noticed there were a lot of Mexican tourists (from other parts of Mexico) and a handful of foreign tourists. City is situated in a really beautiful large valley that's got volcanoes and mountains off in the distance on all sides. Mild weather. Rained every evening for a couple hours, but otherwise sunny during the day. Suprisingly cold at night, actually.
I cannot compare it to Monterrey or Guadalajara, havent' been to those two.
I would like to return to Puebla and spend a little more time there.
I voted for Puebla. I've been to both Guadalajara and Puebla, but not Monterrey.
I think Puebla has better weather. It gets hot in Guadalajara. I also thought Puebla had better food and history, and a nicer downtown core. One can also take day trips to Cholula, as previously mentioned. I also felt things were a bit cheaper in Puebla than Guadalajara. Mexico City also isn't too far away.
Guadalajara was hot and smoggy when I visited. I didn't find the sites within the city terribly interesting (Hospicio Cabanas, Mercado Libertad, etc.) I also took day trips to Tlaquepaque and Tonala. I went to both on non-market days so there wasn't much to do. However, Guadalajara does seem larger and more youthful/energetic than Puebla.
My understanding after reading the responses is that Puebla is the most historically linked of the three cities. I also get the impression that it has a much more intricate pedestrian environment and a whole lot of vibrancy.
All three appear to be superb cities, all more urban than any in America with the exception of New York and maybe Chicago and Los Angeles.
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