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I'm gonna categorize things, as that's how I would want to see my info while planning. These are just in order of how they came to me and not of importance.
Comfort
Pillows: Sure, hotels and motels have pillows for you, but you have to be there to use them. I recommend everyone bring at least one pillow. If you have room or a demand, bring more than one. Being able to nap or just get a bit more comfortable in the car goes a long way.
At Least One Pair of Lightweight Footwear: Comfort is important while on a trip. You want to be able to have something to wear while you're just moving in and out of the car, hotel/motel, or even walking around most indoor attractions. Breathability and lack of weight can help keep people from dropping down into "grumpy pants territory," while on your trip.
Safety
Trip Planning