I drove my Jeep from Alaska to South America, because I wanted to.

In all, I drove 65,000km (40,000mi) in 22 months, through 17 countries.

Without a doubt, actually leaving was the hardest part.

I highly recommend such a trip.

All my stories and photos are at http://theroadchoseme.com

For anyone wanting to do something similar, http://wikioverland.org has all the logistical information you'll need (borders, paperwork, gas prices, etc. etc.)

Edit: I'm in the early stages of planning the next one, which will be bigger :)