The best times of the year to visit Milan, Italy, are April through early-June and September through early-October. During these months, the temperatures outside will be at their best — not too hot, not too cold. It also avoids the rainy season of late fall, starting in mid-October.Outdoor activities and all kinds of festivals are held, and you can even catch women’s fashion week in September. You don’t want to travel to Milan during August because many locals take a month-long vacation and leave the famous city nearly empty.