Aug 12, 2026
July and August get all the attention, but they are also when the islands are hottest, priciest and most crowded. The ferries run full, the good tavernas need booking, and the midday light is flat and harsh.
Late May to mid-June and September into early October are the sweet spot. The sea is warm enough to swim, the hill paths are still green rather than scorched, and the low sun in the evening turns every whitewashed lane gold. Prices drop, rooms open up, and you can walk into a taverna at eight and get a table by the water.
Our small-group island trips run in those shoulder windows on purpose. If your dates are fixed for high summer, aim for the smaller islands where the crowds thin out and build your day around an early swim and a late dinner.