Let me just make a quick disclaimer. I'm on my final night of a one-week visit to beautiful San Miguel de Allende, a lovely colonial city of about 60,000 in the 6,500-foot-altitude mountains 200 miles northwest of Mexico City. This is no tropical resort getaway, as I've had to explain to a number of friends who assumed I was off to some sultry beach locale when I announced plans to spend Thanksgiving in Mexico with a friend. San Miguel is incredibly sunny, but it's dry and fairly cool, too, especially in winter, when it dips into the 30s at night. On the plus side, the mercury climbs into the 70s on most winter days, and in summer, when it can be stiflingly hot by the sea, San Miguel remains fairly temperate.
I used to live in - and still return often to - Santa Fe, New Mexico, which has a similar, although even cooler in winter, climate. If you've been to Santa Fe, you have a good sense of the overall feel and vibe of artsy, sophisticated, and gay-friendly San Miguel. I love it here. I rented a spacious and inviting casita at Casa Carly, a secluded little compound with its own terrific cafe, where my friend and I enjoyed breakfast each morning. Our week-long stay cost us just $500 - back in Santa Fe, a casita comparable to this one would have cost at least twice as much for a week, and possibly even $1,500. In addition to the charm of San Miguel, it's also a terrific value. If this sounds like the sort of place you're seeking this winter as an antidote to rainy or snowy weather back home, I strongly recommend San Miguel de Allende, and there are several other gay-friendly inns and B&Bs in town, plus a number of fine hotels.
I'll admit I didn't spend too much time out partying - this is the kind of town I like to relax in. Although we did venture out each night for a number of terrific meals, including one of the best Thanksgiving dinners I've ever had (please don't tell my mother), at the supremely welcoming restaurant, Food Factory. Don't let the name scare you off - it's set inside a former textile mill and factory, Fabrica La Aurora, that now contains fine art galleries and boutiques, plus a few restaurants.
I did check out a few nightspots, however, and with this in mind, I've written an article on the best gay-friendly bars, clubs, and nightspots in San Miguel de Allende.

I own a house in Guanajuato, about 90 minutes from San Miguel, but I bought some of my house furnishings at the boutiques in Fabrica La Aurora. The quality of handicrafts is wonderful–many people who retire to San Miguel and Guanajuato fill their homes with handicrafts from this area. This is a great place to retire to, btw–great temperate climate, beautiful city, friendly locals, and enough expats that it’s easy to make friends.
Thanks for the comment – my next visit, I plan to spend some time in Guanajuato!