Late winter and early spring is a wonderful time to visit as you will have no problems finding vacancies. If you're staying in downtown Chora during this time, many of the restaurants and shops are not open as they would be during the height of the summer. My friends and I happened to be staying here when Earth Hour was happening, during which many residents put candles leading up to the ruins overlooking the city. A near-spiritual experience. If travelling by ferry from Athens or a nearby island, it is an experience in itself.