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June, July, and August are Kalamata's most popular months. The weather during this time is roasting and dry and the sea temperature is just perfect. The beach will be on everybody's mind so go early and prepare for some competition to get the best spot.
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.