We might spend a couple weeks on Crete (late Aug-early Sept) and really like the Chania (LGSA) area. How difficult would it be to get permission to base a plane there for a few weeks? My experience at Megara suggests tha everything is possible (especially when dealt with in person).
Chania is difficult because it is a military airport and requires a special upfront permission to operate as foreign aircraft. It is now operated by Fraport. There is no AVGAS. You will have to go via a handler.
No 26 here: https://www.aopa.gr/en/flying-in-greece
Ughh.. Fraport… maybe we’ll do Sitia instead, just fewer interesting villas for rent in that area. Open to suggestions. We’ll be 4+ adults + 4 year old child, and maybe some drop in friends.
I would suggest that the eastern end of Crete is much more beautiful than anywhere else there. OTOH some would say there is “less going on”…
I wouldn’t give up lightly, maybe the parking is still cheap and you’re only hit with handling once.
Greece is the place where it can take 45 minutes and 5 pages of paper for a total amount of 1.67 € (I had that in Iraklion) 
I would put it on the Heraklion airport and drive to the West and the Southern Coast. A typical car costs € 30/day in Heraklion (Skoda Fabia etc.)
I go to Crete 1-2 times every year for 15 years now, and there are no nicer places and beaches than on the western part of the southern coast. And itS really only a 2 hour drive, and maybe some ship, depending where you want to go.
