Have you already seen the Ewan McGregor movies?
Long Way Down
There is also
Long Way Round. (http://www.longwayround.com/html/lwr_dvm.html - broken link)
Those guys were very methodical in their preparations, and of course things still went wrong every now. Of course, it's not like you'll be traveling with a film crew.
Still, it's interesting to watch the dvd or read the book; they plot their route and find just the right equipment etc and then, once they are out there traveling, you see what actually takes place.