Oh I could go on for days here, but here's a few of my favorites tips & tricks for making a road trip that is the adventure rather than just a road trip that just gets you to a destination.
Step 1: Don't Set the Stops in Stone
Don't set the stops in stone. A couple summers ago, I'm driving through Northern CA on some dirt road when I see a sign for Lava Beds National Monument -- a place I'd never even heard of. If I had made plans for that night, I probably would have passed on by to "keep to the timeline," instead I went cave exploring and found a motel down the road for the night. With apps like HotelsTonight and Priceline, you can find a place to stay pretty much as you pull into a city.
Step 2: Bring a Sleeping Bag and Perhaps a Tent
To build off my first point, a great road trip is about sights and if you're off the beaten path, being able to pull over in a national forest, cough up $5 and pop a tent for a few hours is a killer option for both budgeting and experiences. Conversely, while little towns can be great to stay in, they can also be dumps... give yourself flexibility, it beats roaches (seriously)!
Step 3: When You Do Make It to Your Destination or a Long Stop, Consider Alternative Accommodations
I don't use AirBnB as often as I should but when I'm going somewhere awesome, I love exploring the properties they, VRBO and similar services have. Hilton is good for work stays, swimming pools and Disneyland but you won't find a $65 / night cabin overlooking a waterfall there.
Step 4: Trucker Stops All the Way
To survive driving all day, you will have stop a few times but where? Pilot and similar truck-driver places tend to be open all night, well lit, fairly safe, heated, have some food option, tons of supplies and lots of (usually clean) restrooms. Beats the heck out of some tiny gas station.
Step 5: Heading Into the Outdoors? Find a Mountain Shop.
Whether it's a local outfitter or REI, mountain shops tend to be staffed by people who play in the outdoors and can tell you where to go and also how to get back safely. Case in point, I was headed to Glacier National Park last month and stopped by Rocky Mountain Outfitters who told me the grizzlies were up... way better to know that in advance than find out on the trail!
Step 6: Traveling With Others? Laptop, Wifi Card, Lock
Driving passes time well, sitting does not. My solve is to plug in, blog about the last adventure or research the next one. When I get there, I have the lock to store the computer safely (and out of sight) in my car or at a coffee shop when I'm solo.
Step 7: Twitter.Instagram.Facebook
While social hasn't filtered down everywhere yet, I've had some great invitations and experiences by connecting up to places along my intended route long before I ever got there. You can even repurpose social meetup / dating apps to connect with local people and avoid the tourist pits.
Step 8: Navigation Screens Beats Phones Once You Leave the City
My car knows where I am at any point and while it may not have Google's updates, I'll take the road direction over no direction. Garmin or a map, always... don't assume you get signal when you leave the main roads.
Step 9: Things to Bring
Febreeze for your car. Twice the chargers your planning on. Single serving laundry detergent packs. A six pack of beer for making new friends. A deck of cards for entertaining said friends. A lot of Advil for when you, and your new friends, have to leave at 6am the next day. A flashlight for when you arrive super late the next night because you didn't leave at 6 or 9 or 11.
And the golden rule: don't pass up the opportunities along the way to explore / try / do something new. Anyone who knows me, knows I have very set ways for most things but when it comes to travel, it's just more fun to see where the road takes you.