We drove from Durham, NC to Cuiaba, Brazil last summer in 29 days (for the World Cup!). There were some ROUGH days, we're talking waking up at 4:30 and basically driving until dark. The biggest problem was trying to hit all the borders right when they opened in the morning and timing your shipping correctly. If you look at the total distance, its about half way, so under 100 days seems totally doable.