
Italy is a popular destination for city breaks, with many iconic and historical cities to choose from. Spring isn't far away and the good weather is getting closer, meaning there's no better time to plan a weekend getaway in Italy. Italy offers a plethora of incredible cities, each with its own unique charm, history, and attractions. Here are some of the best city breaks in Italy, so that you can enjoy an Italian city break or weekend getaway in 2025, beyond Rome, Milan, Venice and Florence.
Where is the best city break in Italy?
Italy offers something for every traveller, from skiing trips to beach holidays. For those with a long weekend, its cities are perfect for a quick cultural getaway, featuring rich gastronomy, iconic sights, and history—ideal for ticking off a city break bucket list. These are our top picks for the best city break in Italy in 2025.
Siena

In Siena, visitors can immerse themselves in medieval charm and history by exploring the UNESCO-listed historic center, highlighted by the magnificent Piazza del Campo, renowned for its shell-shaped layout and the towering Palazzo Pubblico. This medieval hilltop town in Tuscany is home to the iconic Siena Cathedral, and with its intricate facade and stunning interior featuring works by Renaissance masters, is a must-see, as is the nearby Baptistery of San Giovanni.
Meandering through the narrow streets lined with medieval architecture, visitors can discover hidden gems such as the Torre del Mangia and the vibrant Contrade districts. Siena's rich cultural heritage, combined with its picturesque setting amidst the rolling hills of Tuscany, offers a truly enchanting experience for travellers.
Positano

Another great place for a weekend break in Italy is Positano, the pearl of the Amalfi Coast, that has fascinated visitors for centuries. It is known for its picturesque setting, with brightly colored houses perched on steep cliffs overlooking the Mediterranean Sea. The town is also known for its beaches, high-end boutiques, and luxury hotels.
Since Roman times it has been a holiday resort, thanks to its position and particularly mild climate. Positano's narrow streets are a series of ups and downs overlooked by colourful houses and shops selling handmade products. The whole town is dominated by the splendid multicoloured majolica (ceramic-tiled) dome of the Collegiate Church of Santa Maria Assunta, which can be seen from several points.
As well as this wonderful church, some of the main attractions in Positano include the main beach, Spiaggia Grande, which is a popular spot for swimming and sunbathing, as well as the Sentiero degli Dei, a hiking trail that offers stunning views of the coast and the town.
Cefalù

Another great place in Italy for a short break is Cefalù, a town located on the northern coast of Sicily, in southern Italy. It is known for its picturesque setting, with a medieval old town perched on a rocky promontory overlooking the Mediterranean Sea. The town developed around its cathedral, which was declared a UNESCO World Heritage Site in 2015.
Some of the main attractions in Cefalù include:
- The Cathedral of Cefalù, which is a Norman-style cathedral dating back to the 12th century, known for its beautiful mosaics and intricate carvings.
- The Mandralisca Museum, which is a small but interesting museum that houses a collection of art and artifacts from the town's history.
- The beach, La Spiaggia di Cefalù, which is a popular spot for swimming and sunbathing, and also for water sports like windsurfing and kite-surfing.
Cefalù is a great destination for those looking for a mix of history, culture, sea, and nightlife. It's a great spot to explore the Sicilian culture and history while also enjoying the beautiful beaches and sea on offer in the area.
Verona

Verona, nestled on the banks of the river Adige, encapsulates over two millennia of history within its fortified boundaries, serving as a poignant reflection of Italy's tumultuous past. Renowned worldwide for the tragic tale of Romeo and Juliet, this magnificent city has earned the prestigious designation as a UNESCO World Heritage Site.
Its palaces tell of a wealthy and powerful past. The perfectly preserved Arena di Verona becomes a temple to opera and music in summer, offering emotional spectacles to the public, who can attend performances and concerts in a truly evocative setting.
Verona is also known for its good food and wine, with traditional Venetian cuisine and good local wines. A place where Roman buildings, medieval streets and Renaissance palaces coexist, Verona, the city of lovers, will win your heart.
Cinque Terre

Cinque Terre is located on the northwest coast of Italy, in the Liguria region. It is known for its picturesque villages and stunning coastal scenery, with terraced vineyards, olive groves, and colourful houses perched on cliffs overlooking the Mediterranean Sea. With this destination you can visit five villages in one go: Monterosso al Mare, Vernazza, Corniglia, Manarola, and Riomaggiore. Each of these villages has its own unique charm and character, and they are all connected by a network of hiking trails and a train line. Following the Sentiero Azzurro (Blue Path) you can walk through them all, enjoying breathtaking sea views.
Thanks to the characteristics of the territory, Cinque Terre is considered one of the most evocative places on the Italian coast, so much so that is has been part of UNESCO World Heritage since 1997.
As well as enjoying the hiking trails, which offer spectacular views of the coast and the villages, enjoy the stunning beaches and coves in the area, which are small but beautiful and perfect for swimming and sunbathing. The local cuisine is also a must, which is known for its seafood and local wines, such as the famous Sciacchetrà wine.
Turin

A weekend break in Turin, often referred to as "the capital of the Alps," offers a perfect blend of history, culture, cuisine, and stunning surroundings. Visitors can delve into the city's rich history and culture by exploring iconic landmarks such as the Mole Antonelliana and the Royal Palace of Turin, while also immersing themselves in the world-class collections of museums like the National Cinema Museum and the Egyptian Museum.
Culinary delights await in the city's vibrant neighbourhoods, where traditional Piedmontese cuisine can be savoured alongside contemporary dining experiences. A day trip to the Basilica of Superga offers breathtaking views of the city and the Alps, while leisurely strolls down Via Roma provide opportunities for shopping and people-watching. With its blend of historic charm, artistic treasures, and culinary delights, Turin promises an unforgettable experience for visitors seeking a weekend getaway in Italy.
Romantic short breaks to Italy
If you're in search for the perfect romantic short break in Italy then look no further, as Italy offers the perfect blend of charm, culture, and intimacy. Whether wandering through the enchanting streets of Venice, enjoying a sunset in Florence with its art-filled atmosphere, or indulging in a candlelit dinner along the Amalfi Coast, Italy's cities and coastal retreats provide a picturesque setting for couples. The country’s rich history, stunning architecture, and world-renowned cuisine create a dreamy escape, with each destination offering unique experiences, from serene countryside escapes in Tuscany to the romantic allure of Rome's ancient ruins.
Tips for city breaks in Italy
For a successful city break in Italy, plan ahead to make the most of your time. Start by choosing a city that suits your interests—some cities are perfect for history and art lovers, while others offer a romantic, unique experience. To avoid crowds, visit popular attractions early in the morning or later in the evening. Be sure to indulge in local cuisine, from pizza to pasta and beyond, and don't forget to enjoy a gelato while strolling through picturesque streets. Lastly, explore beyond the main sights—hidden gems like quiet piazzas or local cafes offer a more authentic experience.