best small-medium sized Mexican town to winter in
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I would examine your health care needs closely. It sounds like you have some chronic condition, perhaps?
The best health care is going to be in the bigger cities. Mexico City and Guadalajara both have an excellent hospital, for instance. It isn't that Mexico has poor health care, it's just that it isn't so universally available. So you will have to balance your health care needs with the size of the city in mind.
I would check out San Miguel de Allende. It is a smaller town in the central highlands, with a great climate and a large expat population.
Not far from there are Guanajuato and Queretaro, both great cities.
A little farther south and west, Patzquaro is an interesting place. It is still in the highlands with a cool climate, but more rainfall occurs there, and it is blessed with an almost alpine environment. By that, I mean that conifers are the dominant tree type. I like this town for it's lack of expats. It is a popular tourist destination for Mexican tourists, but has been unaffected by outside tourism and has an "authentic" feel, if you will.
I have spent a great deal of time in Mexico, but nearly all of it was spent in the central highlands. Hope this helps.
Gracias
The areas with the most expats will always be the priciest places.
My choice would be either Patzquaro, for it's local flavor, or Guanajuato for it's vibrant nature.
Guanajuato has two hospitals, that I know of, one near the central district, not far from the Mercado.
I think a road trip is in order for you. Spend several days in each town, do a lot of walking, and ask lots of questions. It is impossible to get too specific from an arm chair perspective, if you know what I mean.
If those places seem too cold for your condition, consider the Pacific coast. The area surrounding Puerto Vallarta is mountainous and you can live on the beach or choose a higher elevation to moderate the summer heat.
If you have any questions, my email is: mjplatt@hotmail.com
I sometimes go for long periods of not being on the blogs.
Feel free to email me directly.
Milton
I'd suggest checking out the Puerto Vallarta area - they have serveral good hospitals and once outside of the main town, e.g. Pittial, Mezcales, and to some extent Bucerias. You won't feel that you are in an expat or tourist area but you'll still be close to good medical facilities.
It has a very small town feel and the center of all activities is El Jardin in the center of town. Expats tend to meet there in the mornings and then later in the day you find more locals. The expats only make up about 10 per cent of the population but they are all around and are mostly people with intellectual and artistic leanings.
Property is pretty cheap and you get a lot more bang for your buck.
The locals are the friendliest of people but you'll need to spruce up or learn a little Spanish. You might want to consider doing a course at one of the many language schools.
And of course I shouldn't forget the many, many festivals. There is always some thing going on. The biggest month for that is September when there is literally something going on every day in El Jardin.
You don't need a car. Taxis are abundant and cheap but you mostly need them if you are being lazy. When I lived in the Atascadero area I used them a lot because its a tough hill climb whereas my fiance never used them. This time I stayed in El Centro because I wanted to be closer to the action and neever used a cab once.
They say Mexicans are noisy but this is a very quiet, relaxed town. I have travelled all over the world and this is where I have chosen to settle.
Well. Have I sold you on it?
By the way don't consider going until April because at this time of year it is very difficult to get a house rental or a hotel room. I don't know why. I think people prefer the climate at this time when it's cooler than summer. But summer is not so terribly hot and in September you can be assured of a refreshing downpour every afternoon which usually lasts about an hour.
If you have any questions don't hesitate to ask.
Also there is an excellent hospital in SMA where most of the expats go. It has grown by leaps and bounds over the last few years and has virtually every specialty covered.
In my opinion Mazatlan is the best spot, has all the big city benifits but still a great coastal spot, great medical care and a lot of expats already living here, especially from your part of the world! Look into it, certainly worth your while!
Chers Andy
I lead exciting home buyer trips to San Miguel. Join me on one of these exciting tours to view and buy real estate in San Miguel.
Living In San Miguel
It does get cold at night. I usually need a sweater or light jacket. Another poster said they saw frost, but I never did. Just the luck of the draw, I imagine.
Best advice is to spend time down there in several locations in the highlands and on the coasts and get a feel for what you like.
Asking people what the best town is in Mexico is like asking them what the best town in the USA is....how many different answers do you think you would get?
I can say this, it would be wise to ignore posts from people who are in the business of selling real estate.
So save up some cash, rent short term, and explore.

Google Mexico and the name of the city or town and you will find more listings than you can ever imagine. If you want to stay cheaply, Google "Hostels" or try this link for starters:
vrbo.com/vacation-rentals/mexico
Here is a link for the place where I stay in San Miguel most of the time when I go there:
tripadvisor.ca/Hotel_Review-g151932-d779888-Reviews-Casa_de_la_O-San_Miguel_de_Allende_Central_Mexico_and_Gulf_Coast.html
It was $40 per night per person, including breakfast, two years ago, but the prices may have crept up a bit.
Not the cheapest, but not stupidly expensive. All rooms have fireplaces. Lilia, the owner, is great.
No, it is not so easy - Knowing someone helps. For instance, when I was thinking of San Cristobal, a friend already there told me about some local Mexican agents and I wrote them - but they do not turn up online on a google search! And I ended up renting through someone...on craigslist...as I did when later on I went to Tepoztlan, after searching vainly on google - I am talking 500 rather than 2000 a month. and these people generally don't have websites...they go on craigslist! Of course there are exceptions; the article in this blog on Catemoco shows up online - but trust me, someone who looks and looks a lot: google is for the well off, which unfortunately I am not!
I have located numerous hotels that were spartan, but clean by searching on Google. I usually budget about $30 to $35 per night, but try to beat that when I can. For instance, in the historic area of Mexico City, I have stayed in Casa de Los Amigos, which is operated by the Quakers. If memory serves, it was about $7 per night. Two more dollars got you breakfast. That was for a bed in a dorm room. They had several private rooms for a higher cost. Maximum allowed stay was two weeks. They host and support peace activists and humanitarian aid workers.
These places will let you stretch your stay while you are exploring and looking for longer term arrangements.
More permanent housing is best pursued on the ground, not through any sort of Internet site.
In Mexico, I have also never had a problem just walking the streets, backpack and all and finding numerous acceptable places to hang my hat.
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