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Spending 2.5 months in South America - how's our itinerary?

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Hey all! Been a couple months since we last spoke :) My friend and I will be spending 2.5 months in South America. Here's what we have in mind, would love your thoughts.

- Sept/Oct for 3 weeks: Moto-tour through Bolivia (we have motorbike rentals lined up)
- Oct for 1.5 weeks: Backpack through Peru
- Nov for 2 weeks: Backpack through Colombia
- Nov for 1.5 weeks: Backpack through Venezuela
- Nov/Dec 2.5 weeks: Backpack through Brazil OR Chile

Given the rough itinerary above, had a couple questions

- How is the weather in these countries given the times of year we'll be visiting each? Any countries we should not consider going to given the general weather patterns in the region?
- As you can tell, we're deciding between Brazil or Chile as our last stop. Given we'll be in Bolivia/Peru/Colombia/Venezuela, what would be a better choice to get the holistic South American experience?
- For a U.S. visitor to these countries, would we need to arrange visas in advance or can we get them at the border? Anybody happen to know the price of each?
- Any glaring issues with this itinerary that you'd consider changing?

Thanks so much!
-Kevin

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