It's more fun when you have no money and no supplies. I had to get back from cali to NYC like that a few years back. Talk about adventure.Fun question, Ista. Well mine would be something close to a beatnik road trip. Just going somewhere with my trusty frame pack(I love that thing), my clothes, all the money in my bank account, a couple of REALLY good friends(tempers flaring when you are looking for a place to sleep doesn't work out too well unless you want to butt heads with someone as part of the experience), my toothbrush and toothpaste, a tent and tarp, and a whole lot of optimism and adventure.
I know my ISTP friend would be a good companion as he is really into the adventure sort of thing. Make sure to bring someone to break us out of our introvertedness once in a while during said trip. Perhaps method of trnasportation could be bus or motorcycles because hoofing it would take too mcuh time and money.