I get asked a lot what is the best time to travel to Italy. From experience, the two best months of the year are May and September. The weather is generally perfect during these times, although crowds can still be at their peak. The summers can be really hot, and of course, they generally don't have central air conditioning in Italy, so it can be quite uncomfortable. However, it you're going somewhere like Sicily, where the beach and water sports are the main draw, then you'd definitely want to go in Summer! If you want to avoid crowds and are looking for somewhat cheaper prices, then travel during off-season, or roughly November through April. It all depends on what you're looking for and hoping to do, but May and September are the best times to travel for the most pleasant weather, in my opinion.
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