I chaperoned my cousin's band trip to Disney in April 2005. We had the BEST time! I was 27 at the time and was in the same band in high school. In fact, the band director was the same and he is more of a friend these days. He told my mom that I was going to be his personal chaperone, calling to remind him that it was bed check time and to remove himself from whatever bar stool he was perched on.
Anyway, we flew down from Philly on a charter flight with another group. The plane was about a 100 years old. LOL We stayed at ASMusic and were there for 4 days. We had a great group of kids and chaperones. The best thing for me was being there with my cousin. The fun thing was that I knew some of the kids and chaperones because their older kids had been in band with me.

The asst. director was my ex-boyfriend from high school and one of my best friends to this day.
The bad...well, some of the kids were a bit obnoxious in the hotel and didnt' want to follow rules. Nothing huge, just the keeping the door open when boys/girls are together, etc Fortunately, they weren't my problem. I was in a room wtih my cousin and 2 other girls. At first they were a little

about rooming with a chaperone no matter how cool she promised I was.

In the end, I was the "cool" chaperone only because I was young. I didn't let them get away with anything and in some ways was harder on the kids because I KNEW the things they would pull.
We had a GREAT time and it was one of my best memories of a band trip. I was in WDW with my favorite cousin (we are super close, she's really my best friend), one of my oldest friends from HS, our fun, cool band director and a group of fun kids! Go, enjoy!! Just be ready for ANYTHING!