Portable DVD players with a few movies.
We have a 7" screened portable DVD player. I think you can get them nowadays for around $200 to $250 or so. I'm not sure how long the battery will last, but I believe it was for 4 to 5 hours (I remember reading...) so at least 2 movies. If you have access to a cigarette lighter, mine came with a plug in for that power source.
Magnetic checkers. Magnetic chess. Magnetic backgammon. Bingo boards with crazy stuff (windmills, dead cows, etc). Travel trivia. Books. Magazines.
Our 7 year old daughter likes the DVD player.
Does he like Matchbox/Hot Wheels cars? Bring some of them. Our daughter plays with her little plastic horses and Polly Pocket dolls on truck trips. Maybe some army men or something similar for boys?
Good luck and let us know how it turns out.
Toby
I love the magnetic board game idea and the dinky cars idea too. :idea2: DVD is not an option for this trip. Maybe I'll encourage him to keep a travel journal (me too) then I can tell about how it all works out when we get back.