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The months July and August have nice weather with a good average temperature. A lot of rain (rainy season) falls in the months: January, February, March, April, May, October, November and December. On average, the warmest month is July. On average, the coolest month is January. December is the wettest month.
The weather in Santorini on May is always good. The average temperature is about 19 degrees. Late in the afternoon and evening it's cold but not too much. Dependants on you and in what weather you are used to (like the country you are coming from). October most of times is hotter than May.