I've gone on a lot of XC trips in Jabirus for deliveries, air shows, etc, and here's my general habit pattern for planning such trips.
1. If you are going along a route you haven't traveled before, do some research ahead of time for several airport options. Several, not just one. You never know when weather/pee break/headwinds/need lunch NOW/ whatever will crop up. I like the small airports, usually no bigger than Class D, very near a town. Smaller places usually mean friendlier people and cheaper gas & hangar rates, but there is a chance you'll get there and nobody is around. I always bring along my walking shoes just in case we have to hoof it. If you really need civilization, aim for a Class C airport and you'll find it.
2. Call ahead at these places and ask for fuel, hangar & courtesy car/taxi/rental availability. I have
never had good luck with Enterprise, by the way. I mean, it wouldn't seem so bad if their commercials didn't gloat about their customer service. Anyway, that rant is for another day.
3. In times where weather or whatever cropped up and I've landed at unplanned locations, it was always an adventure, and people always seemed to go out of their way for me. I can't tell you how often "that one dude" happened to be the last one on the field and offered a ride or an empty hangar out of the storm. I guess I've been just lucky. Or maybe being a girl has something to do with it.

Although this has happened a lot when I fly with the guys too.
4. When you fly along a familiar route (I could fly from Tennessee to Florida or Wisconsin with my eyes closed) I always land at places I know are good, especially when solo. Usually the airports with nearby food, friendly people and a courtesy car of good character are the ones that get plugged into the GPS first. One of my favorite spots is Moultrie GA (KMGR). We would swarm that place with Jabirus and Lightnings as our gaggle went to Sun n Fun and Sebring each spring. When you call 5 or 10 miles out, someone always answers from the FBO with a weather report and a "Welcome to Moultrie!" and then we'd ask if the Battle Wagon was available. That's their wonderful old Caprice station wagon. (Or was it a Crown Vic? It's a boat, anyway!) And they have homemade cookies and Mountain Dew. (and I thought Coca Cola owned Georgia.) Another one was Gainesville FL because they have a Holiday Inn with a great bar/restaurant and a free shuttle van. It's the little things that draw the pilots!
VAF is a resource I'm just beginning to discover for planning and help getting out of a jam. It always amazes me how many people respond to calls of help on here.
No matter what, an adventurous outlook and a flexible schedule are required!