Without wishing to sound precious, until I was 25, all flights had been with a pilot I knew! {grin]
My mother worked for a private executive jet charter company, and if the client wanted to fly (for example) from Paris to Munich and back again, it meant the plane was "empty" from Heathrow to Paris, so we would go along for the ride!
Meant we had a day in Paris, mooch about, have lunch etc.
Also just for fun, my step father had a motorised glider, Fournier RF5, if I remember correctly, lovely 2 seater little thing, sat one behind the other,perspex roof which locked with the sort of bolt you would have on a toilet door! 5 point harness, he used to take me flying over the countryside on days off from school, doing barrel rolls and other aerobatics.