I rode a bicycle from Canada to Mexico (in about a month) with a close friend. We bought a book called Bicycling the Pacific Coast (before smart phones).
I had a cheap $150 univega bike and my friend had a $3000 cannondale. His broke mine didn't :)
We were amateurs. We hitchhiked to a bike shop near San Francisco to fix it. Had some saddle bags with our tent and sleeping bag, clothes and water.
It's very doable. Hardest part is just showing up.
America, definitely doable. He's got that cart and he's going through civilization as much as possible, so long as you do time it reasonably there shouldn't be any major problems. Darian Gap, though, wow! Likewise, the Bering Straight.
I had a cheap $150 univega bike and my friend had a $3000 cannondale. His broke mine didn't :)
We were amateurs. We hitchhiked to a bike shop near San Francisco to fix it. Had some saddle bags with our tent and sleeping bag, clothes and water.
It's very doable. Hardest part is just showing up.