Trento - one of our top cities for a winter city break in Italy

Winter City Breaks in Italy

News Travel & Tourism Travel in Italy

Winter city breaks in Italy offer a different perspective on the country’s charm, with many places revealing unique atmospheres and a quieter, more relaxed vibe. Here are ten Italian cities that become especially enchanting during the colder months.

Venice

A quiet canal in Venice during the winter
A quiet canal in Venice

In winter, Venice transforms into a misty, surreal wonderland. The absence of crowds lets you explore its iconic sights at a relaxed pace. Visit the grandiose St. Mark’s Basilica with its shimmering mosaics, and don’t miss the intricate interiors of the Doge’s Palace. The small islands nearby, like Murano, offer intimate glass-blowing demonstrations.

Food & Drink: Warm up with risotto al nero di seppia, a black squid-ink risotto. Pair it with a glass of Soave, a crisp white wine from the Veneto region, or enjoy some Prosecco.

Tip: If you’re there in February, Venice’s famous Carnival offers a spectacle of elaborate costumes and masks, creating an unforgettable winter experience.

Matera

Matera is a UNESCO World heritage Site. Shown with a dusting of snow
Matera, city of caves, with a dusting of snow

Matera’s ancient cave city, known for its “sassi” districts, is like stepping back in time. The historic cityscape, especially under a light winter mist, feels almost magical. No wonder it’s a cinematographer’s dream location. Wander through the maze-like streets, explore the rock-hewn churches, and stop by the Casa Grotta di Vico Solitario to see how families once lived in cave dwellings.

Food & Drink: Try cavatelli pasta with tomato and red pepper sauce, a local winter comfort food. For wine, sip on Aglianico del Vulture, a bold red that complements the region’s rich flavours.

Tip: Matera’s unique landscape often has fewer tourists in winter, giving you a more intimate experience of this UNESCO World Heritage Site.

Trento

Trento Square
Credit: Steve Sloj https://creativecommons.org/licenses/by-nc-sa/2.0/ via flickr
Trento main square. Credit: Steve Sloj

In the shadow of the Dolomites, Trento offers a picturesque setting with mountains that are perfect for winter sports. The medieval Castello del Buonconsiglio and the frescoed walls of its town centre provide a wonderful insight into the region’s history. Trento’s famous Christmas market, with its alpine specialities and handcrafted items, adds extra cheer to the season.

Food & Drink: Try canederli, bread dumplings served in broth, or indulge in a slice of apple strudel. Pair your meal with Teroldego Rotaliano, a local red wine that complements the hearty flavours.

Tip: If you’re into skiing, Trento is a great base for nearby slopes, making it ideal for combining culture with outdoor activities.

Florence

The quiet side of Florence
Ponte Vecchio during the quiet hours

Florence in winter is less crowded, letting you fully appreciate its Renaissance charm. Start at the Uffizi Gallery, where works by Botticelli and da Vinci come to life in the quiet atmosphere. Wander through the Piazza della Signoria, admire Michelangelo’s *David* at the Accademia, and explore the quieter Boboli Gardens for scenic views.

Food & Drink: A bowl of ribollita, a hearty Tuscan vegetable and bread soup, is a local favourite in winter. Pair it with Chianti Classico or finish with a sweet Vin Santo and cantucci (almond biscuits).

Tip: Many Florentine museums offer reduced prices or even free entry on certain days in winter, allowing you to explore more for less.

Lecce

Lecce 
Credit: Paulacastelli, CC BY-SA 4.0 <https://creativecommons.org/licenses/by-sa/4.0>, via Wikimedia Commons
Lecce, known as the ‘Florence of the south’

Known as the “Florence of the South,” Lecce’s Baroque architecture and milder winter make it a fantastic winter escape. The Basilica di Santa Croce, with its intricate façade, is a highlight, along with the Roman amphitheatre and the charming old town.

Food & Drink: Try ciceri e tria (a pasta dish with chickpeas) or puccia, a local sandwich stuffed with meats or vegetables. Pair your meal with Negroamaro or Primitivo, two robust Puglian wines.

Tip: Lecce’s old town is particularly atmospheric with lights during winter evenings, creating a warm and welcoming glow over the city’s white limestone buildings.

Verona

Verona Christmas Market
Credit: A Currell https://creativecommons.org/licenses/by-nc/2.0/ via Flickr
Verona Christmas Market. Credit: A Currell

Verona, the city of Romeo and Juliet, is a romantic winter destination. Visit Juliet’s Balcony, explore the Verona Arena (especially stunning if there’s an opera performance), and stroll through the lively Piazza delle Erbe. In December, the city hosts charming Christmas markets, adding a festive spirit to its historic streets.

Food & Drink: Warm up with bollito misto, a mixed boiled meat dish often served with various sauces, perfect for cold weather. Pair it with a glass of Valpolicella or Amarone, two celebrated red wines from the area.

Tip: Visit Castel San Pietro for panoramic views over the city, especially enchanting as the city lights sparkle below in the crisp winter air.

Orvieto

Close up of Orvieto Cathedral
Close up of Orvieto Cathedral

Perched on a hill in Umbria, Orvieto is striking in winter, with fewer visitors to disrupt its medieval charm. The Orvieto Cathedral’s Gothic façade, the Pozzo di San Patrizio (a medieval well), and the old town’s winding streets all deserve exploration.

Food & Drink: Try umbrichelli, a local pasta often served with a black truffle sauce, perfect for winter. For wine, Orvieto Classico is the region’s pride—a crisp white wine that pairs well with the hearty dishes.

Tip: Orvieto’s underground city tour is fascinating, revealing tunnels and caverns that have been used for centuries for various purposes.

Taormina

Amphitheatre at Taormina with the snowcapped Mount Etna in the background
Amphitheatre at Taormina

For a warm winter getaway, Taormina in Sicily offers mild temperatures and views of Mount Etna. Explore the Greek Theatre, with its sweeping views of the Ionian Sea, stroll through the Villa Comunale gardens, and enjoy the peaceful beaches.

Food & Drink: Savour caponata, a rich vegetable dish with aubergine and tomatoes, or indulge in arancini, deep-fried rice balls with fillings. Pair with a glass of Nero d’Avola, Sicily’s popular red wine, or an amaro, a traditional herbal liqueur.

Tip: If you’re lucky, you might catch a glimpse of Mount Etna’s snowy peaks, creating a unique backdrop for your coastal adventure.

Bolzano

Bolzano Christmas Market
Bolzano Christmas Market

Iin the South Tyrol region, Bolzano offers an alpine winter experience with a mix of Italian and Germanic culture. Visit the South Tyrol Museum of Archaeology to meet Ötzi the Iceman, then wander through the town’s Christmas markets for festive crafts and mulled wine.

Food & Drink: Try speck, a local smoked ham, along with gulaschsuppe, a warming goulash soup. Bolzano is known for its Lagrein and Gewürztraminer wines, perfect accompaniments for the local alpine fare.

Tip: The surrounding mountains make Bolzano a wonderful base for day trips into the Dolomites for skiing, snowshoeing, or simply enjoying the snowy landscape.

Sorrento

Aerial view of Sorrento
Aerial view of Sorrento

With its mild winter weather, Sorrento is a delightful base for exploring the Amalfi Coast and Naples. Stroll through Piazza Tasso, visit the historic Cathedral, and admire views of the Bay of Naples. The town is quieter, and local shops and restaurants remain open, creating a welcoming atmosphere.

Food & Drink: Sample *gnocchi alla Sorrentina*, a baked dish with tomato sauce and mozzarella, perfect for cooler days. Finish your meal with a glass of locally-produced limoncello, a lemon liqueur that’s both refreshing and warming.

Tip: Take a day trip to the nearby Isle of Capri or explore the Pompeii ruins. You’ll find both are quieter in winter and offer a unique experience without the usual crowds.

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