My wife and I did Monterey a few years back. It was a blast. I think it was an anniversary so we were like 45? I remember the staff trying to hype up things "READY!!!" "LETS GO!!!!!" Etc. I am immune to hype, I was on a submarine and felt totally safe with the skydiving crew, no trepidation so no need for the hype. There is an altitude limit that the companies are supposed to jump from (correct me if I am wrong) and everyone in the plane including my wife jumped - I was left alone in the plane with the last 2 instructors and the pilot. Shift in clouds if I remember correctly, but the a hole opened up. Being ex-military I could sense the "Thanks for coming to happy fun time skydiving adventure" rhetoric for 99% of paying customers was quickly replaced by "It's a beautiful day, damn, we should jump from higher but we have this "civilian" on board." I forget what the conversation was but I remember them being excited to jump from a higher altitude - the only problem was me - and I looked at them, swirled my finger in the air, and said after a few winks - "Higher!" They were stoked, don't know how many laws we broke but that was an awesome experience. We dove through a hole in the clouds. Fantastic. Go make a memory Have Fun! Answer from dancurranjr on reddit.com