Fitzroy prefers fall, when the countryside has enjoyed a robust season and is gratefully winding down its tourism trappings, while making the most of the season’s best produce. She says: “It has to be autumn, especially early October, when it’s still warm enough to have a final dip in the sea, to eat lunch al fresco, and feast on the first of the season’s white truffles and the new olive oil. The colors of the landscape are at their best, with scorched fields returning to their vivid green.” By this time, the summer crowds have dispersed, she says, and one will have an easier time navigating the cities as well—she notes queues for the Vatican and other heavily-trafficked sites are reduced. Fitzroy adds, “Visiting in late April and May is glorious, but be prepared for a much colder swim!”
What is Italy’s winter like?
Speaking of the cold, coastal destinations are best avoided during the dead of winter. From October until April, these places largely shut down—you may feel like a genius for booking a cheaper trip during the shoulder season only to arrive and find nothing to do but aimlessly wander from shuttered shop to deserted beach and back again. Yiull notes that she doesn’t encourage clients to hit the coast during colder months, despite fewer crowds (and expenses), because it’s generally true that you get what you pay for—so be ready for trickier weather and less liveliness.
Fitzroy does sing the praises of the Italian fishing village in winter, however, noting that towns with robust industry tend not to clear out in colder months as the resort-based ones do. “Towns that spring to mind are Sciacca in Sicily, Cetara on the Amalfi Coast, and Porto Santo Stefano on the Tuscan Coast. I’ve always adored being in a seaside town out of season,” she says. If your heart is set on hitting the coast during a winter trip to Italy, an active fishing village is your best bet to experience some bustle and life.
It follows Fitzroy’s note on autumn in the city that winter should be an excellent time to hit spots like Rome, Florence, and Venice–an added bonus being the beauty of holiday preparations in early December. The cold (almost always mild in Italy) is often an asset in urban areas; Yiull flags that Verona, Ferrara, Parma, and Milan are worthy visits during the winter. There’s also the Northern mountains for winter sports—the Dolomites get bountiful snow for skiing, and Trentino is home to the United States Olympic ski team.