While I've got the log book to hand (see RN Chipmunk thread), I guess the oldest I've flown solo is the good old Chipmunk (WB671), whilst Bulldog XX513 was a much younger beast (at least in 1979 when I flew it). As a cadet I was privileged to fly in Shackleton AEW2 WL747 in 1974 and was given a brief chance to actually fly it in a gentle circle (seems daft now but I felt 10 feet tall then!). I think one of the most memorable (but only as a pax) was a trg flight trip in 216 Sqn Comet IV XR395 in April 75, shortly before the Sqn disbanded. A few trips in CFS Vickers Varsity WJ945, WL671 & WL670 in 1970 & 71 were also memorable if only for the smell of that old bus! Alas, only a pax then!
