Hi guys,
Just a little intro: I got hooked into motorcycle travel 3 years ago after college and have done some extensive sport-touring around North America and have always had the desire to travel further. I did Mexico last year and am doing Alaska this summer. Mexico was fantastic and now the fire is stoked for riding further south.
I recently came up with a plan on how I can manage a ride to South America. Biggest issue is finding the time off, since even 2 months is too short for this trip. So I've decided to quit my job here in Chicago next Spring (sell everything) and start a new job in Europe in Fall of 2009. This will give me about 5 months for this trip

. I'm from India; been studying/working in the US for the past 9 years and have seen a lot of the US and figured a change of scenery is in order
Now, I know the seasons are reversed because of the Southern Hemisphere and most of the ride reports I've read have people leaving here in the Winter of the North to ride through Summer in the South.
This is my rough idea of the trip and wanted to see how weather plays into it:
Depart Chicago last week of March 2009
Ride down Central America, ship across gap to Colombia
Ride Venezuela, Colombia, Peru, Bolivia, Chile
down to TGF, up to Beunos Aires and end the trip in Rio de Janeiro in the last week of August, where I will ship the bike to Europe to start a new life
Now I know TGF is going to be cold say around end of July, beginning of August, but is it doable. Temps seem to be in the 40sF. I'll have heated gear along. Also, am concerned regarding the high passes in Chile and Argentina during their Winter.
I figure the temps in the tropical region wont change much between seasons but I know I'll have to track the rainy seasons to see if I can avoid them.
Basically, is this trip doable, weather-wise?
Moi, riding down to Batopilas, Mexico last Fall: