We have chartered in Greece twice, once on a 31 footer, just the 2 of us and a few years later with 2 of our children on a 42 footer. Both holidays were idyllic although during the first we encountered some nasty weather near Amorgos, an island we had been warned to stay well clear of!
Mooring stern to isn’t too traumatic if you know the length of your anchor chain. It was a case of third time lucky at one harbour as we laid the anchor too far away from the harbour wall. The locals waiting for our lines were very patient.
We both love Greece. We have friends there and visit many times a year. The thought of spending many years sailing around the islands is very tempting.