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the question of "Why not in October?" was answered in your parallel thread "Greece (Saronic Islands) in October".
In October you don't have the (strong northern wind) meltemi but a high possibility of strong southerlies with stormy weather along, to which most of the protected harbours and anchorages are exposed. Experienced mariners know in advance where to go, not starters without any knowledge of the local conditions, who it seems that you are!