My first trip without the parents landed me in London with a 5"x5" printout map of the city. With that in hand and no plan in mind I ventured forth. Within a few months I was in Greece with 14 countries under my belt and 10 times that many stories to go with them.
My first parentless trip would have been a ski trip to the Poconos in Pennsylvania. A college friend's parents had a time share, so 7 of us went down for a week of skiing. We took two cars, one guys Toyota Celicia and a car we'd borrowed from someone's parents - a Cadillac with a gold grill and gold luggage rack on the back. It had a white leather interior, and sitting in the car was more comfortable than sitting on my living room couch.
One of the guys was Scottish, and by the end of the week I was speaking with a Scottish brouge. Rolling my R's, lassy.
Honeymoons are very popular in the Poconos, so we got a cabin with a red, two person jacuzzi tub.
I bought myself an East Strousburg University T-shirt, and was amazed that they didn't have sales tax.
At the base of the ski hill one day, the radio was playing "Two Princes" by the Spin Doctors. As the song ended, the DJ said how much he loved that song, and wished he could play it again. "Hey, wait a second," he said, "I am the DJ. I CAN play it again." And so he did. Now whenever I hear that song, I think of skiing in the Poconos.
When we were leaving I realized that didn't have proof of Canadian citizenship. I had to drive across the border in the car that didn't have the Scottish chap, because we were afraid they would ask us for ID and I wouldn't have any.
All in all, the skiing was bad but the trip was fun.