It could work for most folks if there were just a few guidelines- a time frame and a general idea of where one might stop and turn around, not to mention a look at the weather outlook.
I'd like to try it sometime, especially in something good for low and slow flying.
Reminds me of Richard Bach's little barnstorming adventure described in his book Nothing by Chance... he just grabbed a sleeping bag and a map and headed out for a few eeks,looking for places to land his Fleet and give rides to people to earn money for gas and food.
The idea was to see if it was still possible to do it the way the old barnstormers did- puttering along mostly with the wind, looking for a town that looked promising, and taking things as they came.
Mind you, he was already seeing a good income from his writing, didn't have to get back to work any particular time, and it was a long time ago when there was more open airspace and farmers were a little more laid-back, but I'm pretty sure he didn't take longer than he'd planned and didn't spend much more than he earned giving rides (beyond fixed costs for the biplane)... even got friends to help him with repairs for free.
It's a must-read book for anyone who likes that kind of flying... he and his friends seemed to have a great time.