As far as roadtrips, I drove to Harrisburg, PA once to pick up a Chevelle for a friend... driving straight through to PA wasn't bad, since we obviously switched off driving, but driving back on 5 hours of sleep sucked.
Drove about 40 hours in a span of 48 (driving insanely slow on the way back).
Those were the days... got a call a few days before, said sure why not... even didn't show up for a part time job so I could take the trip. Good times.