wow you guys are hard-core! My parents are uber-protective, and would probably prefer that I not get on planes alone now (I am 30!). The first time I flew alone - much to their chagrin - was ORL-DTW when I was 20.
They were so nervous about me flying by myself that my father flew with me to Paris 6 weeks earlier to make sure I landed safely and then stayed for a week to make sure that I continued to be safe... what a joke once he realized that no one in France wanted to speak to him in English when I was able to speak in French.
The trip home was exciting -- I came to the airport the night before, since the metro and OrlyBus didn't start running early enough to get me to the airport in time for my flight. There was a boy scout troop also camping there, excited to go to a jamboree (I had no idea that those were real!). They were from some small village a few hours from Paris, and were so excited to meet a "real live American!" -- I felt so special! I learned a bunch of French boy scout songs and they gave me a delicious packet of mentos as I left in the morning.
My father moved from India to London (alone) around the age of 20, and my mother joined him in the states when she was around 20 (again alone). Both of my sisters made their first big solo trips also around the age of 20. I guess that's our family tradition.