Flew into Skiathos many times in B737-200 and -300 and it was always very straightforward - ok the runway is relatively short but is quite adequate so long as you are in compliance with performance A and you fly the a/c correctly!
Madeira is however quite different - potential windshear and curved approach to the north easterly runway. Ok yes I know they have extended the runway which helps. Have flown the B 737-200 in there when the runway was circa 4,500 ft before the first extension and I can tell you that was fun!
But yes i agree flying to the Greek Islands especially when the weather is gin clear is fun in any a/c. Been a while since I have been down to that part of the world but in the early 1980s it was quite common to be held high on descent as ATC was all procedural. My record was FL 270 overhead Rhodes and cleared for approach - Gear Down plus Speedbrake one orbit and then the umbrella approach (all the way to flaps 40) in the B 737-200 and you could descend 1,000 ft for one (yes thats ONE) nautical mile. That sort of flying teaches you a lot about your a/c and how to manage the approach. It's more common these days for people to look at you sideways if you mention the idea of doing a visual approach!
Fly Safe and enjoy Greece!
PS If you want another interesting one try Mykonos - we had to land there with enough fuel to get back to Athens as there was no high pressure refuelling there in those days! The runway was about 4,500 ft so you wanted the weight as low as possible for landing performance but needed to get in with about 5 tons to make it to Athens - my sort of operation, what flying is all about!