By Alison Fox
July 28, 2019
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The sun was starting to wane one fall evening, and while the air had a slight crisp bite to it, we had settled at a table on the balcony in Milan anyway.

A scarf wrapped around my neck, I sipped an Aperol Spritz — the only respectable cocktail for aperitivo when you’re overlooking the gothic-style spires of the Duomo (and the most popular drink of the summer) — and realized I liked it better when it wasn’t screaming hot out. I’m not alone.

Not only is the cheapest time to go to Italy during the fall and winter, it’s also one of the most pleasant times. And the cheapest way to get there is through Milan, Liana Corwin, a consumer travel expert at Hopper, told Travel + Leisure.

“September is going to be the best time to go if you're still trying to get in that summer-ish season,” Corwin said. “What we're seeing is travelers flying into Italy should try to fly into Milan and then travel to other cities from there.”

Demand for flights to Milan from the U.S. (in comparison to other international destinations) is up 12.5 percent this year from 2018, according to Hopper’s flight search data. And the flight prices are trending down: prices are down 21 percent for Milan for September 2019 compared to September 2018, according to Hopper.

In September, the average price for a roundtrip ticket to Milan is $807, Corwin said. That will be slightly higher if you fly into Rome (you’re looking at about $850 roundtrip) and even more if you fly into Naples (a little over $1,000 roundtrip).

While September is a popular, yet still inexpensive time to go, the colder months tend to be the absolute cheapest. On average, Hopper found flights as low as $513 roundtrip to Milan in February or November.

Meanwhile, if you’re flying out of Miami you’re in luck: it’s the cheapest city to fly to Italy from, according to Hopper’s statistics, with an average low price of $554 for flights from July to September. That’s followed by New York’s JFK airport where the average low price was $563.

Flight prices vary by route, but Corwin said the surest way to get a good deal is to start tracking prices early, keeping track of the cities and destinations you’re interested in going to.

And if you needed yet another reason to head to Italy during the cooler months (besides the fact that it’s winter truffle season), the mild weather is certainly convincing. In Rome, temperatures tended to fall in the high 70s or low 80s in September last year, according to AccuWeather, while January tended to be in the mid-to-high 50s.

While no one can deny that basking in the warm sun on the Amalfi Coast is a perfect way to spend a day in the summer, it is equally as wonderful to stroll through the winding streets with a cioccolata calda — or hot chocolate — in hand.

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