I'm with Pete on the head camera video thing. There's too much country to see, and who wants to pfutz around downloading, editing, archiving, etc. for 2-3 months?

If he's going for the ride, make sure he has a nice point and shoot camera. Something like the Olympus Tough series might work well; it'll fit in a jersey pocket and be readily available, and since it's waterproof, no worries about rain or sweat.

I've been looking at some of the super-zoom (20-30X) lens P&S lately, but I'm not sure about keeping the camera steady with a 350mm effective lens.