The island is bigger than you think kastri. If I were you I would give myself more than 10 days. You will need a day to drive from one end of the island to the other........and another one to drive back again at the end of your holiday. That doesn't allow you a lot of time to get a 'feel' for anywhere, let alone both ends of the island.
I guess that by October you might even have some properties to look at? - Viewing will also take a 'bite' out of each day! The good thing is that in January there will be plenty of letting properties available. - Many summer holiday lets are rented out for longer in the winter months. You should get something like that from January until April.....which might not be a bad idea. A shorter let would allow you to look around more areas once you arrive in January.