Where to go from early November through late March in Latin America?

Posted by joshua0005@reddit | Shoestring | View on Reddit | 10 comments

I want to visit Latin America during these five months. I have a total budget of $15k, excluding flights. I speak fluent Spanish and I can get by in Portuguese so I do not want to go to extremely touristy places like Puerto Vallarta and Cancún.

I prefer slow traveling (1-2 months per city). This is because I am traveling partly to escape winter (I live in the Midwestern USA) and partly because I loved living in Latin America the first time I went. I want to go to three different cities in three different countries.

I already know that I want to visit Buenos Aires for two months and somewhere in Brazil and I'm not sure if Buenos Aires would be better in November and December or February and March.

I'm not sure about the third country and I'm not sure where in Brazil but I'd like to do 1.5 months in both locations and I don't want to spend any more than $1.5k USD a month if possible but I can go up to $2k. Here is what I'm looking for in these cities: