The best destinations in Italy for a city break

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Looking for a skiing holiday, summer sizzle or glamorous cruise? The Italian landscape is preened for every season on the travel calendar, but none more so than the time-short and culture-hungry traveller’s favourite – the perennial city break.

Famed for its rich regional gastronomy – think bowls of bolognese, wood-fired pizzas and scoops of gelato – Italy’s cities have all the ingredients to tick off sightseeing, culture and history from a city break bucket list.

Tourists may first be drawn to the rustic glamour of the capital, but it’s not just “when in Rome” – the Mediterranean country is a tapestry of ancient ruins, rolling hills and timeless art from boot to heel.

Harbourside island hubs in Sicily in Sardinia blend beach days with Baroque architecture, while Naples and Milan compete to polish the edges of their authentic offerings into holidaymaker-friendly hotspots.

From Renaissance Florence to coastal Cagliari, here are the best cities to visit for the ultimate Italian experience.

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Milan, Lombardy

Once a key player in Italy’s industrial Golden Triangle, Milan has remained a frontrunner in finance and high-end fashion. You’ll notice there’s no shortage of brand names in the dome-topped Galleria Vittorio Emanuele II. However, the northern city is not without old-world charm, from the operas and ballets of Teatro alla Scala to the grand paintings in the Pinacoteca di Brera museum. Not forgetting the ornate Duomo di Milano cathedral with sweeping city views. Even better, all these sights are easily reached via the Campari-coloured tram network.

Where to stay

True to Milan’s industrial roots, Nnow Milan is housed in a former electrics factory with a fashionable twist. The hotel brings splashes of orange and purple to its modern, minimalist rooms. It also boasts a a quirky rooftop pool terrace, Turkish bath and Italian bistro in the same style.

Catania, Sicily

The unsung star of Sicily, Catania sits at the foot of active volcano Mount Etna. It has an ancient Baroque centre, trattoria-littered squares and dramatic natural wonders that tick all the boxes for an Italian city break. If that isn’t enough, Sicilian street food staples include arancini and ricotta-filled cannoli. These tempting treats can be enjoyed by travellers taking the cable car up Etna, exploring ruined amphitheatres and admiring the facade of the Cattedrale di Sant’ Agata. Don’t miss the festivities in February when the Festival of Saint Agatha commemorates the Sicilian patron saint with a parade of relics, music and a feast.

Where to stay

On Via Crociferi, one of Catania’s oldest Baroque streets, Crociferi B&B is a Sicilian hideaway with frescoed ceilings, sea-view terraces and antique accents. On the breakfast menu, homemade cakes, juice, jam and cold cuts fuel days spent exploring the old town.

Florence, Tuscany

Tuscany’s compact capital still thrives in the Renaissance riches of the creatives it once hosted, from Michelangelo to Dante. With a riverside horizon of Tuscan hills on one side and belltowers and domes on the other, chic Florence has also made a name for itself on the shopping scene with luxury leather stores and designer brands dotting the streets. Galleries including the Pitti Palace and the Basilica di Santa Croce showcase timeless art masterpieces and, the third largest church in the world, The Duomo, is an unmissable Gothic landmark with a famous Florentine flair.

Where to stay

At 19th century residenza, Antica Dimora Johlea, six high-ceiling bedrooms exude warmth. Rooms are designed in traditional Tuscan style with coloured silk drapes and the roof terrace has enviable views of landmarks on the Florentine skyline.

Bari, Puglia

On Italy’s coastal heel, Bari is a port city where buzzing nightlife and balmy beaches meet the traditional culture of Puglia. In the old town, known as Bari Vecchia, you’ll find impressive churches including the Basilica San Nicola cathedral, as well as a Strada delle Orecchiette pasta street and the artsy Piazza Del Ferrarese square – all scattered between elaborate Italianate buildings. For dinner, it’s got to be focaccia and fresh fish rounded off with a palette cleansing gelato from local loved Gentile.

Where to stay

Atipico B&B offers the Barese experience up steep steps in an old town cul-de-sac. In the B&B, three cosy, rustic rooms, each with a TV, fridge and balcony, epitomise space-saving for a compactly comfortable short break in Bari.

Cagliari, Sardinia

Cagliari, Sardinia’s capital, sparkles on a curved Mediterranean coastline with 25 centuries of heritage to discover – plenty to fill a short break. The harbourside city, home to the steep lanes of Castello, the Giardini Pubblici formerly royal gardens and flamingo-populated Poetto Beach, is cloaked in legends, and a lack of light pollution makes it the ideal place to spot constellations – ideally with a Sardinian sausage sandwich in hand.

Where to stay

Undeniably, breakfast is best from a rooftop terrace with harbour views. At Marina Di Castello, one of Cagliari’s most elegant B&Bs, four spacious and modern rooms invite guests to tuck in for the night and for sweet pastries just steps from the Via Roma main street.

Rome, Lazio

The Italian capital spills over seven hills – it’s an open-air museum of fountains, ruins and Renaissance echoes. With a tangle of enduring landmarks including the Colosseum and Pantheon still firmly on the map, remnants of Ancient Rome are wonderous must-sees for city breakers visiting the Eternal City. Carbonara by the bucketload, cappuccino breaks and vista point picnics on Aventine Hill are encouraged during days spent, undoubtedly, on sightseeing overload.

Where to stay

In lively Trastevere, Hotel Santa Maria – once a 16th century convent – hosts characterful terracotta rooms set around a charming courtyard of citrus trees, just a short walk from the centre of Imperial Rome.

Naples, Campania

Often disregarded as Italy’s ‘gateway’ to the citrus-studded Amalfi, a Naples city break quenches the thirst for local authenticity with a rugged energy that’s less shiny than the tourist-preened likes of Rome and Venice. The birthplace of pizza isn’t without its own big hitters. There are Unesco-listed Greco-Roman streets in Centro Storico, Napoli Sotterranea – an underground labyrinthine of tunnels – and the Quartieri Spagnoli Spanish Quarter, perfect for sipping an Aperol spritz on long Napoli weekends.

Where to stay

For personable tranquillity on the hillside of Vomero, family-run B&B Weekend a Napoli is a home from home. The Art-Nouveau villa comes complete with a patio garden and authentic Italian breakfast spreads, all just 200 metres from a metro station.

To trace Caravaggio’s footsteps, travel through Naples and bring his greatest works and dark past to life