Turns out Porsche Cars North America CEO Klaus Zellmer has already done the most American thing possible, road tripped an Oldsmobile Delta 88 from Los Angeles to New York. John Snyder with Autoblog was able to dive into the story with the surprisingly approachable executive.
Zellmer arrived in the U.S. with a friend from school after graduating college in Germany. The two were out to see the world, or at least the U.S., with only two aluminum suitcases and $1,000. They made their way to a used car lot and showed the stack to the salesman. He walked them to the back of the lot and showed off a weathered Oldsmobile. It started, so it was theirs.
The two took the car across country and after three months, they finally made it to New York, where Zellmer was eventually able to settle down.
Moral here is: if you don't have a road trip story yet, go out and find one.