Posted on 27 September 2021

Planning an Italian city break? Buona idea! - the only problem is, which one to visit?

Blessed with more UNESCO World Heritage Sites than any other nation, you'll be architecturally and artistically spoiled no matter where you choose. The same goes for the food.

Here are our top 10 picks for the best Italian city breaks.

Florence

The capital of Tuscany invites a flurry of superlatives - all of them well-deserved.

While relatively compact and walkable, the cradle of the Renaissance is filled to bursting with beautiful cathedrals, piazzas, and art galleries. In terms of concentrated attractions, it represents one of the best short breaks in Italy.

The main church is the Duomo (Santa Maria del Fiore), whose mighty terracotta dome can be seen from across the city. Consider a stroll up one of the surrounding hills to enjoy its full majesty.

Battistero di San Giovanni is another must-see basilica. Although called a "minor basilica", its octagonal shape and famous bronze doors with relief sculptures are world-renowned.

Less than 10 minutes' walk from San Giovanni is the medieval Ponte Vecchio - the only Florentine bridge to survive extensive redevelopment efforts by the Luftwaffe. Aside from World War Two, the bridge has survived several big floods, making it one of Florence's best-loved landmarks. Peruse the many jewellery shops on the bridge, which have been here since the 1600s.

Food-wise, Florence can compete with Italy's best. Alongside the usual (often fabulous) pizza and ice cream, there are some Tuscan specialities to try: Potato tortelli, chicken liver pâté and lampredotto (the fourth stomach of the cow!).

Rome

A Roman holiday seldom disappoints, such is the depth of the Italian capital's historic and cultural treasures. Remnants of the city's 3,000 year history are everywhere. 

Must-visits include the Colosseum, Roman Forum and Pantheon, but you'll stumble across ancient and baroque masterpieces everywhere - from fountains to monuments to churches.

You'll wonder how so much of it survived the rigours of history.

If you can afford it, book a hotel close to the Pantheon, which places you right in the heart of the historic action.

But a visit to Rome is just as much about living "la dolce vita" - the sweet life. Romans are living proof you don’t need to run around like a headless chicken to live a contented existence - lounging at a pavement cafe or enjoying evening aperitivos is just as critical.

You’ll only scratch the surface on a short city break, but Rome remains one of the best places in Italy for a weekend getaway.

And you’ll surely be coming back for more.

Venice

Now could be a perfect time to visit Venice, which has seen the tourist numbers slump due to the pandemic.

A quieter city will make it easier to appreciate the grand dome of San Simeon Piccolo, St Mark's Square, and numerous Gothic palazzi.

Aside from being a quintessential Italy city break destination, right now hotels are also considerably cheaper due to lower footfall. At time of writing you can bag a room on the Grand Canal for as little as £80.

Outside the main tourist draws, there are plenty of vibrant neighbourhoods to explore - offering a more contemporary side to the city. This year, the 17th International Architecture Exhibition is taking place here, running until November.

Milan

At first glance, Milan can seem a little grittier than Rome, Florence or Venice, but it boasts plenty of cultural attractions, including the Duomo, the Scala opera house and the Pinacoteca di Brera art gallery. It's also home to Da Vinci's The Last Supper, housed in the wondrous Santa Maria delle Grazie.

However, most visitors come to Milan for the shopping: high-end outlets are found across the city, but the largest agglomeration is located in the fashionable Quadrilatero D’Oro district.

If you find yourself skiing in the Italian Alps, make some time for a visit to this vibrant city, many of whose treasures remain undiscovered by Britons.

Note that a visit to Milan comes with a higher price tag than most Italian cities, but the pandemic means you'll at least get some hotel bargains.

And for Brits, it’s one of the best places in Italy for a weekend away, at just under two hours by direct flight.

Positano

A visit to Positano is usually undertaken as part of a wider exploration of the stunning Amalfi Coast.

While the city is known as a bolt-hole for the super-rich, beyond the stately villas and gleaming yachts there's a more authentic culture to discover. Farmers tend modest, precipitous plots that cascade down the hillsides, while fishermen still make a humble living from the sea.

Highlights of the town include swimming and sunbathing on Positano Spiaggia Grande, strolling down Fornillo Beach, and taking a boat trip to La Fontelina.

But perhaps the best pastime is to dine at a restaurant overlooking the Tyrrhenian Sea as the sun goes down.

Orta San Giulio and the Italian lakes

Orta San Giulio is the perfect base from which to explore the legendary Italian Lakes.

The Romans, keen to escape the Imperial capital, first identified the Lakes as a great place for a few days off empire-building.

The views here are among the finest in Europe: The breathtaking Alps sweep down the Lakes Garda and Como, where a vast tourist industry has evolved.

But while hotels and restaurants are usually full (notwithstanding pandemics), the beauty of the area remains intact.

Aside from Lakes Como and Garda, make time for Lake Maggiore and the lesser known Lake Iseo to the east.

You'll see more if you hire a car, but you can also explore by public transport: plentiful ferries connect the towns and resorts across the awe-inspiring lakes.

Palermo, Sicily

Boasting more than 230 ancient churches, no less than 12 UNESCO Heritage Sites, the third-largest opera theatre in Erie, and four ancient street markets, Palermo has an almost overwhelming supply of architecture and culture.

Paid tours are a great way to ensure you don't miss the main attractions, but if following the herd isn't your thing, you can always build your own itinerary.

And when it comes to food, the options are equally diverse. Choose from cassatas, cannoli, ice cream, pizza, and seafood. Vegetarians are well catered for too, since Sicilans consume a great many legumes.

Palermo arguably represents one of the best Italian city breaks, thanks to its surroundings.

Wider Sicily offers the volcanic island of Stromboli, the Valley of the Temples (comprising eight Greek ruins), plus plenty of clean, beautiful beaches - such as San Vito Lo Capo.

Bari

The largest city of the Adriatic, Bari is the perfect staging post for exploring the Puglia region.

While it doesn’t have the architectural grandeur of Lecce or Brindisi, Bari is a more modern, forward-looking city, with a more vibrant nightlife.

That’s not to say Bari is lacking in historical attractions. You find the bones of St Nicholas (aka Santa Claus) in its Basilica di San Nicola, while the archaeological museum gives a fantastic grounding in the area’s rich history.

Beyond Bari, the fabulous architecture of Lecce beckons, with its bigger hitter, the Basilica di Santa Croce. Near Andria is Castel del Monte, a uniquely octagonal castle, while the tiny limestone houses of Alberobello, with their famous conical roofs, are more than worth a visit (they're UNESCO-listed).

Perugia

Umbria's largest city boasts a medieval centre that has barely changed in 400 years; a beautiful huddle of cobbled alleys, stairways and piazzas. The calm beauty of this ‘centro storico’ masks the city's bloody past.

Aside from the many churches and Gothic mansions, Perugia offers a superb nightlife, fuelled by the large student population which, come the evening, fill up the cafe terraces and jazz haunts of the city.

Further afield, the atmospheric hilltop town of Orvieto awaits, along with Assisi, Gubbio, Todi, Spoleto and Norcia. These towns have made Umbria increasingly popular in recent years, although it’s still off the radar compared to its neighbouring region, Tuscany.

Umbrian scenery is at least as pretty as that of Tuscany, typified by olive groves, vineyards and cypress-covered hillsides.

Cinque Terre

These five historic, vibrant villages are among Liguria's prime attractions, spaced as they are along the region's fabulous coastline.

A UNESCO-listed area since 1997, Cinque Terre is certainly on the tourist map, but don’t let the throngs put you off - these fishing villages, perched precariously on the cliff sides, will lift even the most morose of spirits. And there are plenty of other less well-known, picturesque villages along this coast, easily making Cinque Terre one of the best short breaks in Italy.

Mercifully, cars are banned here, with public transport taking the form of a 19th century railway line whose coastal tunnels ferry around local and tourist alike.

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