Sounds like fun to me. My dog loves car rides and is used to 5 hr drives almost every weekend. As long as you stop enough to let the dog out for exercise and toileting - of course it's good for you too if you take a break, plus it gives you time to take in the scenery and hopefully enjoy the ride more.

I would be way too nervous about sending him on a plane. I heard on the news it is more expensive now (don't know if that's true) plus here on the east coast we're having a little heat wave in the 90's so I would worry about cargo temperature.