First time I said good-bye to my mom and dad was when I was 16 years old. I left for 11 months (on good terms). I wouldn't say I was alone ever - but that was when I learned to create a support network for myself no matter where I go, no matter what language. After that, I started to crave having the rug pulled out from under my feet and continue to do what I can to keep things shaken up.
Age 16 :: I used to take embarrassing selfies with dictionaries...
Didn't hitchhike, though, until I was 20. Used that as my main form of transportation for a while along with riding the ferry.
Although, I did just settle down for the winter in Alaska because my friend had a baby and I pretty much want to just snuggle that kid as much as possible...