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From June through to August, Santorini is filled with sunseeking holiday makers who fly into the Cycladic Island to relax in its high temperatures and bask on sunny shores. During these months the Aegean Sea is at its warmest and there's plenty of entertainment to be found in the lively bar and restaurant scene.
Visit Kalamata in September or October and you'll avoid both the busiest months of high summer and the peak prices that go with them. September and October are only marginally cooler than August and the sea has not yet started to cool down. You'll have a lot more elbow space in the Old Town and on the beach too.