We started the trip out by dragging him out of bed before 6am and hoping to get him to stay asleep. He stayed asleep until I had him all buckled into his car seat and then he opened his eyes and smiled. For the entire first hour on the road he didn't make a peep, and he didn't have a single toy. Just resting, I guess. I was giddy with optimism about how far we would make it on Day 1. Then he had a small coughing fit that resulted in him puking all over himself. We pulled over, cleaned him up, and he was ready to soldier on. (We made it to Bologna by 6pm, where we were able to explore and enjoy the city a bit before going on to Tuscany the next morning.)
To keep him occupied in the car, we had small cars, a few books, and......an ipod touch in case of emergency. He had a few games and a few videos on the ipod, and we let him play with it when his patience with sitting in his car seat ALL DAY was starting to fray. Everyone was happy. We also listened to some new Swedish music we got with Astrid Lindgren songs, including Pippi. We got a lot of Pippi requests throughout the trip, and I think Martin thoroughly enjoyed singing along to his childhood favorites.
My attitude going in was that we would probably have to take some long stops to let Simon and out and stretch his legs. On our way down (12 hours) we stopped twice. On the way back (2 6 -7 hour legs) we stopped once. He definitely has the Herwig road trip genes. We took long road trips growing up (ie. MN-> Key West) and we too were built for the road.
Looking forward to the next one with my road trip ready family!