I admire you. I was over sheltered, never had to do anything for myself. When I graduated from high school I was in Brazil with a US diploma which was not recognized there (did it on purpose so that the only option I had was return to the US, to a state I had been to before to ski, but I had been to Boulder only once. One of the reasons I picked University of Colorado was because if my parents didn't approve of something it would take them 24hrs door to door to stop me.
I did get kicked out of school my Freshmen year for playing/exploring too much. I made up my mistake during summer school. I had a wonderful time and met wonderful people. As long as you pick a place that calls to your heart you will be fine.