Possibly the most well-known and popular extreme road-trip is the famous "Cape to Cairo." You drive from Cape Town, South Africa to Cairo, Egypt (or vice-versa.) It doesn't matter which way you go, rather that you drive all the way across Africa. There is some scary terrain along the way, and you're sure to run into some dodgy, dangerous situations. This is also what Land Rovers and Toyota Land Cruisers were specially designed for. This one is definitely on my list of things to do oneday, but I think I would prefer to do it via motorcycle. This is THE extreme driving classic.