We have been on multiple flights and road trips with our 4yo and we'll be driving for our next trip. We flew for our trip in Nov and while I enjoyed the shorter travel time, I hated stressing about what I was bringing and how much my suitcase weighed. I like to bring a lot of stuff to make our hotel room comfortable (fan, nightlight, pillows, blankets etc) and its so convenient having the car if we need to run to the store for something. Plus, if we're driving we can be more flexible about when we leave. I've even conned DH into adding extra days onto our vacations...if I can score a good priceline express deal while we're there I'm going to try and do it again in September! Our drive is about 16 hours and we're splitting up 9 hours and 7 hours. I don't book a hotel until we're on the road so if we think we can go longer we will. Having a shorter drive on arrival day is nice. I will download a bunch of stuff on the ipad (movies and new games), plus we have this travel tray that attaches to the car seat if she wants to draw or play with toys. Snacks are also hug! I'll get her favorites and some that she doesn't get very often like fruit snacks. I've also tried to find playgrounds along the way to help burn some energy. One time, we even stopped at a zoo for a couple of hours!