Since you are a Colombian, expect below Peru and any altitude in Los andes, very cold weather. Never freezing temperatures at low level except Chile, Argentina and evrything below and in between. It could be a warm winter or could be a freaking cold winter. For this God have the answer.
To tell you the thruth, it is the worst time of the year for the Andes and the southern cone countries.
The Andes (Ecuador, Peru, Bolivia), have dry season on these month, which is good for the ride but it will be cold. As for the Andes on hte southern countries better to check the conditions at the borders between countries. They could be closed because of the snow or gelid temperatures.
As for southern Chile, expect rain every single day up to August. Beginning September the spring start showing up and better temperatures.
My 2 cents, never ever cross the Andes after 4pm or sleep in tent overnight. It could be fatal.
Venezuela and Brazil to be the almost end of the rainy season, but expect heavy showers and sometime impassable dirt roads. However , most of the main roads connecting both countries are paved.
Atacama Desert is fine dry and it never rain but it is extremely cold after 6pm and during the night. Most of the nights and early in the morning you'll find a lower fog that make difficult to see the road in front of you. It is very thick and not fun, beside for being dangerous. Well, most riders don't ride at night right?.
Everything is possible, but not like with good weather. Just keep checking the weather condition every week, be well dress for the ride. Have heating devices in your steering and body. Take an Aspirine every morning and protect your neck and face.
South America it is cold over the winter in the high latitudes but rarely below 0 C degrees, so it is somehow better than in the U.S. , except in the high Andes.
I 've ridden from Boston to Miami in winter with 25 -30 F degrees and I've sustained the ride without problems, except at late night hours. So it is possible down there with a little of an effort. If I was doing your trip, I will avoid Chile and Argentina during winter. Instead I would spent more time up to Bolivia and Peru which both have a lot of landscape to show and ride. Leave Chile for another time, from November to March is a paradise.
GastonUSAChile screwed with this post 04-04-2013 at 08:30 PM