Italy's best travel months are May, June, September, and October. They're also the busiest and most expensive time to visit (with the north remaining just as busy throughout midsummer). Crowds aside, these months combine the convenience of peak season with pleasant weather.
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Winter is the perfect time to visit Italy's best cities – personally, as a local, on my own vacations, I avoid visiting places like Rome, Venice and Florence in any other season, because I can't deal with the crowds. Rome in winter is a really great place to visit.
Italy's best travel months are May, June, September, and October. They're also the busiest and most expensive time to visit (with the north remaining just as busy throughout midsummer). Crowds aside, these months combine the convenience of peak season with pleasant weather.
“Aside from winter travel, shoulder season (March through May and September through November) is known for cheap Italy deals,” he shared. If you can hold out until the end of the spring shoulder season, you'll be rewarded with pleasant temperatures in the mid to high 70s across the country, according to WeatherSpark.
Italy and Greece have very similar weather and seasons. Warm and sunny from May to October, cool and wet from November to April. Greece does have a slightly longer summer and beach season (especially in the southern islands).
Spring and autumn are the ideal seasons for sightseeing in Italy: not only are all attractions open but you won't need to stand in long queues to enter (like in summer) and you'll have fewer crowds to contend with. Winter is also a good time if you're thinking about hitting museums and galleries.
If your time is limited, you'll be able to see Italy's highlights in a matter of days—but spending two weeks or more means you'll get to explore multiple regions and fall in love with authentic Italy.
Rome in winter is one of our best-kept secrets. Most of the season, you will enjoy the city like most visitors never get to: (almost) all to yourself. Arch of Constantine in winter sunshine - chilly but sunny, and look how uncrowded! But there are lots of great reasons to enjoy winter in the Eternal City.
Tuscany's actually worth a visit in all seasons, for different reasons. While you won't be able to lounge on Tuscany beaches or cycling in Chianti in short sleeves, there are an incredible amount of activities on offer in the chilly winter months.
All in all, Spain is generally a bit cheaper to visit when choosing an Italy or Spain vacation. Restaurants and hotels are mainly more affordable, even in larger Spanish cities like Madrid, Barcelona, and Seville. Note that you will use euros as currency in both Italy and Spain.