The Best Time to Visit Italy for Beaches, Sightseeing, Fresh Olive Oil, and More

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For city sightseeing: winter and early spring

If you’re anything like the average traveler, the combination of stifling heat and elbow-to-elbow crowds can be a sightseeing buzzkill. So if Rome and Florence are on your agenda, the best time to visit Italy will be January, February, and March, when the crowds are much more manageable — so long as you’re there after New Year’s and before Easter. In both cities, the weather during that time can vary from bright, chilly, and sunny to cold and rainy, though snow and truly brutal weather are unlikely in either place. In Rome, especially, the absence of crowds makes the winter months a fine time to explore the city. In the northern cities of Venice and Milan, the weather will be less cooperative and could be foggy, rainy, and bone-chillingly cold thanks to the humidity. But you’ll likely find the iffy weather a fair trade-off in exchange for the elbow room, especially at top-tier attractions like the Colosseum, the Uffizi Gallery, or in Venice’s narrow passageways.

The downside to city sightseeing in the winter is that it gets dark early — by 5 PM or so on the shortest days — and outdoor attractions will adjust their hours accordingly. But that’s just an excuse to start aperitivo hour a little sooner.

Where to stay for a winter city break

Where you stay can shape your entire winter city break — especially in Italy’s historic centers, where the right base puts you within walking distance of everything you came to see. In Venice, that might mean a quiet apartment tucked along a canal, close enough to wander home from a foggy morning stroll through Piazza San Marco. For more options, check out Matador‘s full guide to the best Airbnbs in Venice. In Milan, you’ll want a place that’s well-connected and cozy, ideally with room to settle in after a cold day of museums and aperitivi — this roundup has a few worth bookmarking. And for Rome, where even the tourist-heavy areas feel calm in winter, staying near the Colosseum lets you squeeze in one more site before dinner — these Airbnbs offer practical access without skimping on atmosphere.

For beaches: June and September

Now here’s a tricky one. July and August see the most reliably hot, sunny days, which means you’re virtually guaranteed some quality time with UV rays and warm (okay, warmish) ocean water for swimming.

But the best time to visit Italy for beach-goers is also the worst time of year for going to the beach in Italy. That’s because all Italians (and a good percentage of Europeans) converge on beaches up, down, and around the boot. Even harder-to-reach destinations, like the remote beaches of Sardinia’s Golfo di Orosei (Gulf of Orosei), are packed. Hotel and vacation rental prices are at a premium, and it’s hard to find a room or apartment without a one-week minimum reservation. Car traffic in beach towns is at a standstill, restaurants are overwhelmed, and beaches have only matchbook-sized sections of free sand. In a word: ugh.

The solution? Book an Italian beach vacation for June or September. There’s still enough of a beachy vibe in these months, minus the masses and high-season price tags. The further south you go, the better your chances of warm weather and seas tolerable for swimming into the fall. In Sicily and on the southern Pelagie Islands of Pantelleria, Lampedusa, and Linosa, it’s possible to swim into October.

Where to stay for a beach vacation to Sicily

Accommodation is also cheaper and more readily available in the shoulder season. For Sicily, if you want to start in Palermo, please, for the love of arancini, choose an Airbnb with character. After a cultural city fix, head to the coast, where you’ll find some of the most jaw-dropping houses in the Mediterranean. Surrounded by meadows of native flowers and ancient olive trees, this boutique villa is one to bookmark. This six-bedroom Airbnb, ranked in the top five percent for quality, offers 360-degree views of the countryside, mountains, and ocean. It’s a prime spot for taking in the dramatic pink Sicilian sunsets over the north of the island.

For mountains: Late spring, June, and October

If you’re not sensing a theme here yet, it’s this: shoulder season. As with Italy’s beaches, the country’s mountain destinations are best enjoyed when everyone and their brother aren’t there. There are two peak seasons in Italy’s Alps and Dolomite ranges: summer and winter. Planning your trip to avoid the busiest periods (July through September for summer sports and December through mid-March for winter pursuits) means you’ll sacrifice a little in terms of weather and trail (or snow) conditions in exchange for lower prices and fewer crowds.

In these northern ranges, you can likely engage in some winter sports into early April, depending on that year’s snowfall and temperatures. This writer lives in Italy and snowshoed at Madonna di Campiglio in the Brenta Dolomites well into April last year.

If you visit the mountains in June instead of later in the summer, you’ll find crispier weather but still plenty of that heart-soaring summer beauty — meadows blooming, brooks a’babbling, and hiking trails shaded with new foliage. It’s the best time to visit Italy if you can plan your trip around outdoor adventure rather than beaches and cities.

In the fall, there’s a shorter window of shoulder-season opportunity, largely because many accommodations and gondolas close from mid-to-late-October through early December. But if you can squeeze in a trip at the end of September or the beginning of October, you’ll have dodged the school-age crowds and be able to enjoy the more relaxed last hurrahs before seasonal closures. (Note that many of the same businesses that close for a few weeks in the fall also close from May through early June.)

If you set your sights farther south to the Apennine Range as it runs through Abruzzo and points further south, take heart: it’s never as crowded there, though winter snow and snowsports are no longer a given.

Where to stay for a vacation in the mountains

In the mountains, where and when you go tends to matter more than in the cities. Some towns stay active year-round, while others all but shut down between seasons. In the Dolomites, places like Ortisei and San Candido stay connected to the trail network even in quieter months, making them reliable bases for early summer hikes or spring snowshoeing. In the Alps, Courmayeur is one of the few mountain towns that still feels lively outside of peak season — and its compact size makes it easy to navigate without a car. And farther south in the Apennines, especially around Abruzzo, you’ll find Airbnbs are more rural and the tourism infrastructure thinner, but the trade-off is a slower pace and fewer crowds than the northern ranges.

For seasonal cuisine: October and November

One of the great pleasures of a vacation to Italy is dining on seasonal, regional cuisine. And there’s absolutely no better time to do this than autumn, when Italy positively bursts with fresh-picked and foraged delights that are either unavailable or just not quite the same as any other time of year.

The best time to visit Italy for olive-oil aficionados is surely fall, when connoisseurs can rejoice at bright green EVOO (extra-virgin olive oil), which, in its freshly pressed form, has a spicy bite to it. Sink your teeth into a piece of bruschetta con olio nuovo (with new oil) and prepare to be transformed. Harvests start in late October, and most olive groves are from Tuscany south through Puglia and Calabria, or on the islands of Sicily and Sardinia. If you buy oil to take home, be sure it’s from the current year’s harvest.

If fungi are more your fancy, fall is also the best time to visit Italy. Autumn’s frequent rainy days, interspersed with sunny ones, create the right environment on the forest floor for Boletus edulis, better known as porcini mushrooms, to spring forth in abundance.

If you’re not in the mood to traipse through the woods in search of your next meal, you’ll find these prized mushrooms in plates of pasta and risottos, as hearty soups, fried as appetizers, or topping meat dishes on menus everywhere throughout the country.

The last of the culinary big three of the Italian autumn are truffles. These underground fungi are known for their pungency and persnicketiness — they’ll only grow in certain types of soil, under certain trees, and in certain seasons and regions of Italy. From September to December, expect to find delicate white truffles from Piedmont, Tuscany, Umbria, and Le Marche being shaved over plates of pasta, eggs, and meat. They’re more aromatic and flavorful and harder to find than summer’s black truffles. And for many foodies bound for Italy, they’re reason enough to make the trip.

Where to stay for seasonal cuisine

If you’re coming to Italy in the fall for the food, consider a farm stay. In Tuscany, Ebbio is one of the better options. The restored 13th-century farmhouse near Monteriggioni doubles as an organic farm and retreat space. It’s run by a mother-daughter duo who grow everything from herbs to olives and host workshops on foraging, preserving, and cooking. Meals are vegetarian and homegrown, served around a long communal table. If you’d rather be near Sicily, the island of Pantelleria, just off its southern coast, is home to Parco dei Sesi — a working estate set within a 5,000-year-old archaeological park. Here, olives and capers are cultivated entirely by hand on four acres of terraced plots overlooking the sea. You’ll dine on meals crafted from the estate’s own produce, and it’s also a convenient base for exploring the island’s hot springs and ancient ruins.