Cortina d’Ampezzo
Sitting pretty in the heart of the southern Alps, Cortina d’Ampezzo is one of the best ski resorts in Italy. Many skiers dream of the opportunity to ski the Dolomites, and Cortina d’Ampezzo offers world-class skiing and snowboarding trails, plus cross-country skiing and snowshoeing. For something a bit different, you can also try renting a fat bike, snowkiting, or even curling.
There are plenty of family-friendly activities at Cortina d’Ampezzo, too. Little ones can learn the pizza/French fry basics at ski school, try ice skating, and go sledding. Animal lovers of all ages will thoroughly enjoy dog sledding and pony rides. And, of course, there are plenty of incredible local restaurants and cafes to fuel up. Tempt your tastebuds with some of the local flavors and signature dishes like spätzle and barley soup, which will surely warm you up on a chilly day. “All in all, the experience blended perfectly the need for adventure and a desire to taste European culture and cuisine,” one reviewer wrote on Tripadvisor.
Trento
Trento is the capital of Trentino Alto Adige, a northern Italian region, and wine lovers might recognize the city for Trentodoc, a Spumante sparkling wine made from Trentino grapes. Nature lovers will also enjoy Trentino, as the region is known for its majestic landscapes of mountains and lakes. It’s also a fantastic area for skiing during the winter months. The slopes of both Madonna di Campiglio and Val di Sole are sure to get your blood pumping.
Whether you choose to ski or not, the views of the Dolomites are nothing short of spectacular here. You’ll be able to see the rock towers of the Brenta Dolomites west of Trento, as well as the “Queen of the Dolomites,” also known as the Fassa. As you explore Trento, you can marvel at the many Renaissance frescoes on the buildings in the historic center, pop into the museums, and warm up in local restaurants, which seem to be around every corner. Christmas markets also make this region come alive during this time of year, so be sure to carve out some time to see the Christmas markets in Trento, as well as in neighboring towns like Levico and Rango.
Venice
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Picture yourself and your loved ones bundled up on a gondola ride in Venice with a brisk chill in the air. Sounds dreamy, right? While Venice is certainly a popular Italian city to visit in the summer, there’s a lot to be said about visiting in the winter. Travelers can expect fewer crowds as they wander around Venice during this time of year, especially in December before Carnival. However, in December, beautiful holiday lights create magical displays in the evenings, and the Christmas markets of Venice would put even the Grinch into the holiday spirit.
The Carnival of Venice is one of the main winter events in Venice. The dates vary since it leads up to Ash Wednesday, but Carnival typically makes February the perfect month to visit Venice (or early March), just like Mardi Gras in New Orleans. Don’t miss the first day, when an acrobat jumps off the San Marco Bell Tower and soars down a zipline to land on Saint Mark’s Square. The whole 10-day event is filled with parades, balls, costumes, and plenty of activities the whole family can enjoy.
Florence
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The capital city of the Tuscan region, Florence in the winter is just as dreamy as you can imagine. Marvel at Renaissance masterpieces, stroll across the Ponte Vecchio (the oldest bridge in Florence), and climb to the top of the Cathedral of Santa Maria del Fiore, also known as the Duomo, for a picturesque view of the city. While Florence is a popular Italian city to visit in the summer, visiting this Tuscan gem in the winter affords you the luxury of fewer crowds and cheaper hotel rates, making the trip a more budget-friendly experience.
In early December, Florence also kicks off the start of the Firenze Light Festival, which is also called the F-Light Festival. This light festival illuminates Florence for about a month. During the festival, the main attractions and historic buildings in Florence are lit up with spectacular lighting effects, projections, and unique artistic installations.
Pisa
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Another popular town in the Tuscan region, Pisa, with its iconic leaning tower, attracts visitors from all over the globe hoping to take that iconic tourist photo. While the UNESCO World Heritage Site is certainly worth a selfie, there are plenty of things to do in Pisa to fill up your winter days. This 1000-year-old town boasts a treasure trove of Romanesque and Gothic churches to tour, plus more hidden gems than you can count.
For a unique perspective on the city, wander over to the Walkway of the Walls. At 36 feet high, you’ll have a grandiose view of Pisa and a dreamy selfie spot. When it comes to the nightlife scene in Pisa, head over to Piazza delle Vettovaglie, which translates to “supply square.” By day, it’s a local market where visitors can stock up on fresh fruits and vegetables, but you’ll find plenty of restaurants, cafes, and wine shops to enjoy as the sun sets. While Pisa is known for attracting an influx of summer crowds, travelers on Tripadvisor report a less crowded experience during the winter months.
Genoa
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This sprawling Italian city in northwest Italy is the sixth-largest city in Italy, so you’ll want to give yourself plenty of time to see it all. Known for its deep maritime history, visitors to this capital city in Italy’s Liguria region may be familiar that it’s the birthplace of Christopher Columbus, and a visit to the seaport is an absolute must. The Port of Genoa is Italy’s busiest seaport, and watching the boats pass through is a mesmerizing sight.
Continue onward to the Galata Museu del Mare, the maritime museum, where you can view Italy’s largest submarine while soaking in even more of Genoa’s maritime history. In a port city like Genoa, you can expect seafood to reign supreme. Speaking of food, Genoa is the birthplace of pesto, so be sure to indulge in some authentic Pesto Genovese while you’re in town. Genoa is also known for its days of New Year’s festivities, which take place in the historic city center and around the Old Port.
Sicily
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If you’re yearning for a much milder winter adventure, this southern Italian city is just the ticket. Italy’s largest island is a history lover’s paradise, with top attractions like the Valley of the Temples, the Cappella Palatina, and the Greek amphitheater of Taormina ranking high on the must-see list. Christmas markets are also abundant here, and you’ll find no shortage of those in cities like Palermo.
If winter beaches are your thing, grab your swimsuit and head over to Cefalu, a picturesque village on the northern coast that’s known for its beaches. While the ocean is pretty cold during winter, with sea temperatures in the low 60s Fahrenheit, some find it comfortable enough for swimming.
Of course, no visit to Sicily is complete without gazing at Mount Etna, the highest active volcano in Europe. This active volcano looks especially majestic when covered in snow. If you don’t want to hike it, you can always take a cable car up. “I’ve been to Sicily in February and it was in the 70’s and gorgeous!!” one reviewer on Tripadvisor wrote, adding, “If you go up to Mt. Etna it will be cold, so bring a heavy sweater!”
Rome
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A visit to Rome in winter is one you’ll never forget. The Eternal City fully embraces the holiday season, and you’ll find plenty of Christmas markets and shopping opportunities within the beautifully decorated city. The winter festivities in Rome begin in December and carry on through January. Unlike some other Italian destinations on this list, winter is a popular time to travel to Rome, so you’ll want to book your accommodations as early as possible. To avoid large crowds in Rome, your best bet is to visit in the shoulder seasons of spring and autumn.
If you plan on visiting Rome in February, prepare to celebrate Carnival. While Venice and Viareggio tend to get all of the Carnival glory, Rome still puts on quite a show with plenty of Carnival events. Carnival in Rome tends to be much more kid-friendly than in other Italian cities, which is something to consider if you’re planning a family trip.
Naples
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Naples is another mild winter city in southern Italy, but be sure to pack your rain gear if you plan on visiting during this time of year. What this city lacks in snow and frigid temperatures, it makes up for in rainfall. Winter is the rainiest season in Naples, but don’t let that discourage you. Even though you may encounter a rainshower or two, there are plenty of indoor activities in Naples to keep you entertained, especially for opera fans.
If you get lucky with the weather, visit Via San Gregorio Armeno, also known as Christmas Alley. Here, you’ll find dozens of local artisans ready and waiting to sell you their handcrafted treasures to take home. During the Christmas season, nativity scenes are a Naples staple.
The crowds can be rather large during Christmastime in Naples, so if you need an escape, rent a car and take a scenic drive along the Amalfi Coast. Marina Grand Beach and Fornillo Beach are both beautiful beaches. While it may be too cold to swim, these are ideal spots to sit for a spell and admire the scenery.
Milan
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Milan is another wet city during the winter months, so be sure to pack your rain gear. Milan doesn’t see too much snow, with January being your best bet for seeing the city in a fresh coating of powder. However, Christmas is a big deal in Milan, and the Piazza Duomo puts up a huge tree with stunningly beautiful lights, and you’ll find delightfully charming Christmas markets scattered around town.
December 7 is the beginning of Saint Ambrogio’s festivities, and since Saint Ambrogio is Milan’s patron saint, expect everyone to celebrate. Also, must-see attractions in Milan like the Duomo and the Basilica of Santa Maria delle Grazie will experience much thinner crowds in winter than during the summer months. This can be incredibly beneficial when visiting popular Milan attractions, such as Leonardo da Vinci’s “The Last Supper” mural in the Basilica of Santa Maria delle Grazie.
Lake Como
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Visiting Lake Como during winter is an unreal experience. While travelers can benefit from fewer tourists and cheaper hotel prices, many of the boat tours and attractions are operational year-round, meaning you’re not missing out when visiting in the winter. Wandering through the area’s iconic villages like Bellagio and Varenna offers unparalleled beauty during this time of year.
The lake villages come to life during the Christmas season, and the light shows are surely going to amaze you. The Christmas festivities, also known as Città dei Balocchi, take place from late November until early January, and it boasts some truly mesmerizing lighting effects in the town of Como. For adrenaline seekers, you’ll find no shortage of skiing opportunities to pass the time. Piani di Bobbio and Valchiavenna are fabulous places to hit the slopes, especially if you’d prefer to ski on day trips versus spending your Italian vacation at a resort.
Puglia
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Sitting pretty in the heel of the boot, Puglia offers endless miles of Mediterranean coastline to enjoy. From the university town and capital city of Bari to the incredible Baroque architecture of Lecce, you’ll never run out of things to do in this southern Italian region. Puglia has been gaining popularity as a tourist destination over the years, and it’s easy to see why. Known for its picturesque countryside, Puglia is also famous for its olive oil production, and foodies will thoroughly enjoy the culinary scene here.
Diving into the center of Puglia, the charming town of Alberobello is a must-see. Strolling through the UNESCO World Heritage Site’s iconic cone-roofed, stone trulli huts will make you think you’ve been transported to another realm. Referring to the trulli huts of Alberobello, one traveler wrote on Tripadvisor, “It is definitely a worthwhile day trip and the experience has somewhat of a fantasy feel about it.”
Amalfi Coast
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Known for its sheer cliffs and rugged shoreline, the 34-mile stretch of coast along the Sorrentine Peninsula in Italy is a bucket list travel destination for many. Visiting this gem in the Campania region during the winter is full of incredible sights, sounds, and smells. Each of the 13 seaside towns is worthy of a visit, and they all have a unique claim to fame. For example, in the town of Cetara, you can visit the Norman tower, which, as legend goes, was founded by Hercules himself.
Positano is the most popular city along the Amalfi Coast. The Mediterranean architecture, combined with the cliffs against that beautiful blue water, is enough to make you consider moving here permanently. If that doesn’t win you over, the town’s beaches will. Marina Grande Beach is one of the most beautiful beaches in the region, but you may enjoy the secluded Arienzo Beach even more. While it will be too cold to swim in winter, the coastal views are spectacular year-round.
Matera
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Known for its ancient dwellings set into stone, not to mention the famous St. Lucia alle Malve church, history lovers can’t pass up an opportunity to visit Matera. Nicknamed, “the second Bethlehem,” this ancient city is just overflowing with historical sights everywhere you look. A few must-see sights in Matera include the Rock Churches of Matera, the Crypt of the Original Sin, and the House Cave of Vico Solitario. The house cave gives you a realistic glimpse of what life was like for the earliest inhabitants. For panoramic views, check out the Piazzetta Pascoli of Matera.
Foodies will not be disappointed when visiting this region of Italy — no matter the time of year. Be sure to try the cruschi peppers, an iconic sun-dried-then-fried favorite. For a hearty meal, the pignata is a must. When visiting in winter, this slow-cooked mutton served with potatoes and vegetables will hit the spot on a cold day. Around Christmas, visitors can also experience the Living Presepio displays in Matera, which are large nativity scenes that involve entire neighborhoods.
