Postcards from Italy

Fall and Winter in Italy: Travel Ideas to Kickstart Your Plans

Whether with tentative garden snail-like feelers or gung-ho “get me out of here now” enthusiasm, Americans are considering travel to Italy again. The country is moving towards opening its borders for leisure travel and international visitors are beginning to stroll through long-empty sights like the Colosseum and Uffizi Gallery in increasing numbers.

If you are ready to shake off your cabin fever with a jaunt to il bel paese, now is the time to start planning and reserving for fall or winter trips. Italy is bracing for one of its busiest periods for tourism from late 2021 through 2022 as the world dusts the cobwebs off their luggage, and the best hotels, most beloved tour guides, hottest museum tickets, and other trip musts are booking up fast.

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Won’t be travelling until 2022? You should still begin putting the gears in motion for your trip sooner rather than later. As Brian says, “If 2021 isn’t your thing, you’ve got to get started now to make sure you’ve got the best of the best planned for 2022.”

Here are some of our favorite fall and winter destinations to get your travel inspiration flowing:

Top Fall Destinations in Italy

The Amalfi Coast

Positano

The Amalfi Coast is one of the most popular destinations in Italy (even last summer in full-blown pandemic the coastline was packed with Italian and European visitors) and visiting during the high-season summer months can be a bit of a chore. You can easily escape the summer crowds by exploring by sea on a private mini cruise, but once you’re on land again, expect snarled traffic, full restaurants, and narrow lanes with people strolling elbow-to-elbow. 

To avoid the hassle of the crowds, just plan your visit for a few weeks into early autumn after the high-season melée has dispersed and, voilà, you’ll find the coastline a peaceful retreat. Temperatures through October are generally warm enough that you can relax on the beach or poolside (and even take a dip, if you’re lucky) or set sail on a private day cruise along the Amalfi Coast or across the water to the island of Capri by speedboat or traditional gozzo fishing boat.

Another perk of a fall Amalfi Coast visit is touring nearby attractions like the ancient ruins of Pompeii, the vulcanic crater atop Mount Vesuvius, or the captivating labyrinth of Naples’ historic center without the searing Mediterranean temperatures that can make day trips in July and August a chore.

Read more about the Amalfi Coast:

Eating Your Way Through Naples and the Amalfi Coast

Where to Stay on the Amalfi Coast: A Town Guide

The Dolomites

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These UNESCO-listed peaks that straddle the border between Italy and Austria are one of Europe’s top ski resorts, but you don’t need to be an enthusiast of the slopes to enjoy this spectacular spot in fall. Instead, you can savor (and photograph) its stunning scenery: explore the vast network of hiking trails; take a scenic drive through the Mis Valley; or hop aboard one of the Alpine train routes (the Renon line between Collalbo (Klobenstein) and Soprabolzano (Oberbozen) on the Ritten plateau is among the most panoramic in Europe).

The Dolomites are also known for their indulgent spa hotels and excellent cuisine that features unique Alpine dishes rooted in the mix of Italian and Austrian cultures for which Trentino-Alto Adige/SudTirol is known. You can choose from an array of Michelin-starred fine dining restaurants or tuck into local specialties like polenta or canederli at a rustic mountain lodge. 

Read more about the Dolomites:

Exploring the Dolomites in Summer

So You Want to Hike in Italy…

Bologna and the Food Valley

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Emilia Romagna is home to Bologna, considered the country’s epicurean capital, as well as Italy’s “Food Valley”—birthplace to iconic specialties like Parmigiano Reggiano, Prosciutto di Parma, and Aceto Balsamico. Fall is the ideal season to visit both the city and the surrounding region, as the season’s milder temperatures are more conducive to the hearty appetite you will need to sample this region’s dozens of local specialites. 

In addition to offering some of the best dining experiences in Italy, Bologna is a delightful city with a wealth of historic and cultural sights, excellent shopping, and a vibrant atmosphere due to the local university, the oldest in the Western world. Just outside the city, the Via Emilia stretches across the region from the beach town of Rimini to Piacenza and connects a series of small cities strung like pearls along the route, including Bologna, Reggio Emilia, Modena, and Parma (also home to the annual Verdi Festival).

Read more about Bologna and the Food Valley:

Parma Food Tour

Balsamic Vinegar Tour

Piedmont

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Another fabulous foodie destination, the Langhe-Roero and Monferrato areas of southern Piedmont are home to some of the most prized truffles and wines in the world, which both reach their peak in the fall. Le Langhe-Roero encompasses the towns of Barolo, Serralunga d’Alba, Alba, and Bra—all known for their excellent DOC and DOCG Barolo and Barbaresco wines made from the local Nebbiolo, Barbera, and Dolcetto red grape varietals. The bordering Monferrato area produces Barbera, Freisa, Grignolino, and Dolcetto red grapes to make equally extraordinary DOC and DOCG wines. If you time your fall visit carefully, you can see how the grapes are harvested by hand in the vineyard-covered hills that turn red as the leaves change color. You’ll also, of course, taste wines from previous harvests in the region’s countless boutique wineries.

The hills of Le Langhe-Roero and Monferrato also produce prestigious white truffles—tartufo bianco d’Alba—and host the annual White Truffle Festival (and auction) in the town of Alba each fall. The local trifola white truffle, known as Alba’s “white diamond” due to its price point and prestige, is in season from September through the winter, so you can taste if fresh grated over local tajarin pasta or mixed with heirloom Fassona Piemontese beef for a gourmet tartare.

Read more about Piedmont:

Hunting Truffles in Italy

A Day in Turin

Top Winter Destinations in Italy

Umbria

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Christmas in Italy has a very Old World feel to it, where family, faith, and—of course—food take center stage. Nowhere is this more true than the picturesque region of Umbria, a quiet corner of central Italy where you can retreat for a peaceful winter holiday and feel like you have the entire region virtually to yourself. Don’t expect the glitz and glam of a holiday in the city, but leisurely days of exploring the medieval hill towns and villages that are scattered across the region, including Montefalco and Bevagna; Assisi, birthplace of St. Francis; and the stately historic city of Perugia.

You can also unwind over long meals featuring the region’s unbeatable extra-virgin olive oil, cured pork charcuterie and aged sheep cheese, heirloom legumes, and bold Sagrantino wine. All of this just a short drive from Rome’s Fiumicino airport, so you can be landed and settled into your village retreat in hours.

Read more about Umbria:

A Day in Orvieto

Christmas Traditions in Italy

Venice

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This winter may be the first and last opportunity we’ll have during our lifetime to see Venice without the throngs of international tourists that generally crowd the city’s main sights. The Floating City has very few permanent residents, so has seemed particularly empty over the past year and probably won’t see pre-pandemic numbers until spring. So book your trip now to savor the city during its particularly quiet winter. 

Though Venice is cold (and damp…that romantic mist comes at a cost) in winter, the benefits of visiting without the crowds far outweigh the extra sweater you’ll need to pack. Most hotels and restaurants are open for business throughout the year, and you can visit St. Mark’s and the Doge’s Palace without the long lines, wander the tiny calli and campi in peace, and glide along the historic canals in a traditional gondola with lap blankets to keep you warm. 

Read more about Venice:

Carnival in Venice

Acqua Alta in Venice: A Survival Guide

Sicily

Selinunte

If you are hoping to avoid the crowds during your first travel forays but are looking for warmer climes than chilly Umbria and Venice, head south to Sicily, set just a few nautical miles from Africa. Though you won’t be able take a dip in the Mediterranean, the island boasts mild winter temperatures that hover around 60° and very little rain, so you can pack lighter and spend more time outside.

Avoid the resort towns along the coast, many of which more or less shutter for the winter season. Instead, explore historic cities like Palermo, Taormina, and Syracuse with their authentic local markets, fabulous art and architecture, and unique cuisine that combines influences from the whole of the Mediterranean basin. The island’s many UNESCO-listed archaeological sites stay open all winter long, as well, if you want to strike outside of the cities to explore treasures like the Valley of the Temples and Segesta.

Read more about Sicily:

Sicily’s Stunning Mosaics

Caltagirone: Ceramic Capital of Sicily

Related posts:

Four Foodie Fall Trips in Italy

Christmas in July: Why Winter is the Time to Visit Rome, Florence, and Venice

Christmas in July: What to Expect during a Winter Trip to Italy

Travel Specialists

Maria Landers

Brian Dore