We drove with a 4 year old and just turned 2 year old this past June from Austin, Texas. My "tips":
1. We don't do much TV at home (no cable--2 half hour PBS shows daily--and one of those is Between the Lions--(former first grade reading teacher here) But on the road trip I say, "BRING ON THE MOVIES!!!!" We brought lots of Disney movies which also helped the kids "know" the characters.
2. I brought a "secret" bag of toys and pulled out new ones every hour or so. Examples:---plastic slinkies, spinning light up Disney toys; travel magna doodles; pipe cleaners to make into shapes, necklaces, etc.; silly putty; fruit loops and yarn to string; small cookies sheets with magnetic letters and shapes (all from Dollar Tree); attached to the cookies sheets--crayons in an altoid can with a magnet on the back for coloring; Color Wonder markers and paper; stickers and paper; felt kids sets; colorforms/window clings to stick on the windows. I guess that's all I recall, but they LOVED having new things to do.
3. We don't drive through the night, either. My kids have never been car sleepers--they just catnap. So we left at 4:00 am. With frequent stops, lunch at Cracker Barrel in Lafayette LA and a tropical storm from the Texas/LA border all the way to Orlando, we made it to Pensacola the first night. Checked in to a Courtyard Marriott by 7:00pm. Then up early and arrived at WDW by 2:00pm next day.
4. For hotel stops, we have always gone with Hampton Inn, Fairfield Inn, and Courtyard. They are less than $100 and all seem to be fairly new and very clean. And, free continental breakfast which easily saves us $20 or so.
5. My other tip that will make some of you cringe. The secret to keeping my 2 year old happy on such a long car trip is an ENDLESS SUPPLY OF CHEETOS!!! We don't "do" junk food at home, so he thought that was the best treat ever!!
6. My four year old who has been reading for a while was also very interested in following our route along on the map, looking for the next state sign, miles to next city, etc.
We really did enjoy the drive as we both hate to fly. And, we were able to pack that van full!!! Brought our own stroller (savings of over $100 versus renting); ice chest, water, groceries, pack n play, you name it!!!
HTH
