As the holiday season approaches, much of Italy transforms into a vibrant, festive Christmas celebration with seasonal antique markets, breathtaking light displays, and the sweet aroma of traditional Christmas cookies and desserts filling the air. 

While the bustling cities of Rome, Milan, or Florence are often the first to come to mind for many Christmas season festivities, excessive crowds can make these cities challenging to navigate. With Christmas being a traditionally Christian/Catholic holiday, both holidayers and Catholic pilgrims flock to Rome and the Vatican for the festivities. 

If you’re looking for a more quaint, serene, crowd-free holiday experience, we invite you to explore some of Italy’s best-kept secrets that locals enjoy each year. We’ll take you on a journey across Italy from the world’s largest Christmas tree to Italy’s “village of wonders” to Christmas in an enchanted castle. 

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From November to January, the northeastern town of Gubbio undergoes a magical transformation and becomes Italy’s City of Christmas. Beneath the world’s largest natural Christmas tree lit on the side of Mount Ingino, the city comes alive with Christmas Markets, life-sized Nativity scenes, and an express Christmas train around the village. 

Located in the region of Umbria, Gubbio is a historic medieval city with cobblestone streets and spectacular snow-capped mountain views, making it the perfect place to spend a holiday without the massive crowds. 

The region of Umbria, also known as the “Green Heart of Italy,” is an excellent place to visit year-round, famous for its world-class wine production, rolling hills, and medieval mountain towns. 

Experience the region of Umbria like a local with a small-group tour! Your backstage pass to Italy awaits, complete with a private, exclusive walking tour of the hillside town of Gubbio on select tours. 

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There’s no shortage of Christmas magic in the Southern village of Locorotondo, located right on the heel of the “boot” in the Southern Italian region of Puglia. Starting in mid-November, the village transforms into Italy’s Village of Wonders, an enchanting atmosphere lit up with Christmas lights as the town fills with local artisans and merchants. 

Locorotondo is widely considered one of Italy’s most beautiful villages, marked by its beautiful dry-stone, white-washed walls, centuries-old olive trees, and trulli houses in the surrounding Valle d’Itria. During the holiday season, the narrow cobblestone streets are often decorated with wreaths, lights, and bows, making this the perfect quaint, off-the-beaten-path destination for your holiday Italian adventure. 

The Puglia region is worth visiting year-round for its stunning coastline, fresh Mediterranean cuisine, and historic cities. Discover it during one of the best times of year to visit when you grab your spot on Passport to Puglia!

Wondering what the best time to visit Italy is? Discover your perfect season!

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Ascoli Piceno

If you’re an avid antique or vintage shopper, Ascoli Piceno of the Le Marche region is the place for you at Christmas time. From December 1 to Epifania, Piazza Arringo is transformed into a Christmas-themed antique market with local products, and food stands with roasted chestnuts and mulled wine, and an ice-skating rink where children can skate with Santa’s elves. 

Living here in Ascoli Piceno, we can attest that Christmas is a state of mind in Italy, complete with month-long celebrations. The piazzas we frequent daily become a festive atmosphere, with Christmas lights and live music filling the air. If you want to experience Italy like a true local, Ascoli Piceno is the perfect place to spend the holidays. And if you want to stay for New Year’s, the Christmas festivities lead up to a memorable New Year’s Eve party under the stars in Piazza del Popolo (One of Italy’s Most Beautiful Squares)! 

Ascoli Piceno is splendid for the holidays, but the rhythm of La Dolce Vita is strong all year round! On select weekends, the antique market continues year-round in one of Italy’s most beautiful squares, making this hidden gem the perfect home base for your stay in Italy. 

Guests with The Italian on Tour stay in a boutique 4-star luxury hotel just steps from fabulous shops, charming cafes, and an artisan gelateria, perfect for quenching your daily gelato craving. 

Ready to sip an Aperol spritz in the piazza on one of our signature tours? Book your authentic Italian Experience today! 

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Bassano del Grappa

Home to Italy’s Oldest Distillery, Bassano del Grappa is the perfect holiday setting for grappa enthusiasts. Grappa is a traditional Italian grape-based brandy with an intense flavor, made with pomace – the grape seeds, stems, and skin leftover from winemaking. 

At Christmas time, the city’s piazzas are transformed into a Christmas wonderland, with a bustling Christmas market open from late November to the day after Christmas and an enchanting train circling the city’s three piazzas

Another popular Bassano del Grappa attraction is the Ponte Vecchio, or “Old Bridge.” This wooden covered bridge spans the Brenta River and has been rebuilt several times since its original construction in the 16th century. Today, near the bridge’s entrances, the cobblestoned streets are lined with jewelry, gourmet food, and art shops. During this season, many shops offer the elixir of grappa to give you a “sip of the Christmas spirit.” 

Looking for more Italian culinary Christmas delights? 

Read the Ultimate Food Lover’s Guide to Christmas in Italy! 

Known for its production of ceramics and pottery, as well as its charming medieval streets, Bassano del Grappa is a must-see for an Italian adventure. Housed in the region of Veneto, the birthplace of Prosecco and home to many historic cities, this city is a year-round attraction that is beloved by locals and charms every traveler that visits it, including Ernst Hemingway who once made Bassano del Grappa home.

On select tours with The Italian on Tour, you’ll visit an artisanal Grappa producer (one of the last of his kind) in the foothills of the Dolomites – and the taste is nothing like the kind you can buy at the store! And if we haven’t quite turned you on to Grappa, you’ll surely fall in love with the wines from the Venetian lagoon, drink top-notch Prosecco in dreamy locations, and visit UNESCO villas where you’ll meet the female winemaker of a historic Venetian family and enjoy a complete tasting of their organic wines.

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Cison di Valmarino

In the heart of the Prosecco Hills, also located in the Veneto region, Cison di Valmarino is home to the Castel Brando, where you can transport yourself back in time to experience Christmas in an enchanted castle! Located between Cison di Valmarino and Follina, this majestic castle is one of the oldest in Europe, a historic treasure in the beautiful Dolomite foothills. 

The historic castle has been transformed into a luxury experience with a spa, restaurants and bars, and magnificent outdoor gardens. 

An enchanted Christmas castle isn’t all the village has to offer – the picturesque town of Cison di Valmarino also hosts their traditional Stelle a Natale Christmas Market (Stars at Christmas) each weekend in December. The winding streets come to life with local artisan vendors and culinary delights. 

Visiting the Prosecco hills is an excellent idea year-round, not just at Christmas time! When you join us on tour you’ll enjoy sustainable bubbly from Cartizze, the top-producing DOCG prosecco, and a local, family-run farm-to-table restaurant. The family produces their own Prosecco from the hills in front of the restaurant, making it a beautiful, unbeatable place year-round, especially when the vineyards showcase their verdant green leaves. And the best part, this hidden gem, is not accessible by buses, which means you’ll never have to worry about the crowds when you grab your seat on any of our Italy trips that take you to Veneto.

Overall, Italy is truly magical during the Christmas season, particularly in these quaint hidden gems where you can escape the crowds. The best part is that you don’t need to venture to the North for the snowy weather to get in the holiday spirit – festivities across the country with milder winters will surely put you in the holiday spirit. And if you can’t make it to Italy during the holidays this year, be sure to check out the Ultimate Food Lover’s Guide to Christmas in Italy to infuse your home with some local Italian traditions or delicious Italian Christmas cookies.




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