Anyone every watched "The Long Way Around" and "The Long Way Down"? Both are available on Netflix. Ewan McGregor and Charlie Boorman ride their BMW motorcycles Starting from London and heading east until they get to New York, and from Scottland to Capetown, South Africa. They have a support team in SUVs following (which is interesting in itself).
Really enjoyable series about phenomenal roadtrips. Everything from preparation and their equipment, the difficulties of bad roads, frequent wrecks, sand, and border crossings. I highly recommend it.