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In the winter, the weather is tempered somewhat by the mountain range located behind the city so although the winters are not severe, it is chilly during that time and temperatures occasionally drop below the freezing mark. It also tends to be rainy during the winter, with periods of heavy fog.
Milan’s high season is July through August, when it is the hottest, and the crowds are the largest. Temperatures regularly rise above 30°C during this time, but there is very little rain. Milan's low season, which runs from November through February, is characterised by unpredictable weather and very few visitors.
In particular, the period from April to June and then September-October are all-round the best. If scheduling a visit during that time isn’t possible, just be prepared for the higher temperatures and the crowds of summer.