Whittling down a list of the most beautiful cities in Italy has something of the Judgement of Paris about it—it’s an almost impossible challenge.
The truth is you could visit almost anywhere in the Italian peninsula and encounter the glamor, style, history, culture, and flair that makes this sunny strip of Europe such an attractive destination.
This article includes the prettiest cities in Italy as well as those that offer a beauty perhaps not as immediately apparent as the Gothic enchantments of Venice or the muscular charm of Rome. Beauty is subjective, often reliant on things like the right light, the right wine, and the right company (thankfully, Italy has these three factors in envy-inducing abundance).
It might occur to prospective travelers that such an attractive headline destination as Rome—the capital of “il bel paese”—might have had the very beauty knocked out of it by so many centuries of self-inflicted eminence.
Fortunately, as visitors awakening in Rome have confirmed when the soft light of dawn illuminates its many treasures, the capital remains one of the most beautiful cities in Italy.
Its immortal elegance arrayed across its seven famous hills, Rome supplies layers upon layers of intrigue and astonishment carefully acquired since its founding in the 8th century BC. The city houses famous landmarks in Europe like the Roman Forum, the Pantheon, the Column of Marcus Aurelius—the list seems endless.
But it’s not all a matter of antique beauty—simply walking the cobbled streets, crossing the travertine-clad bridges, and admiring the lingering sunsets quickly educates as to why Paolo Sorrentino chose to call his Oscar-winning film about Rome, The Great Beauty.
Spend at least three days in Rome and let the city seduce you inside and out, whether you’re gazing at Michaelangelo’s masterpiece within the Sistine Chapel or the triumphant tiers of columns on the Colosseum’s exterior. One of the most beautiful cities in Italy? Of course—and also the most charismatic.
Umbria is a landlocked province in central Italy that’s often referred to as the country’s “green heart”. Bisected by the Tiber on its journey to Rome, it’s a favorite with Romans (it’s a two-hour drive from the capital) who see its pristine wilderness and remarkable destinations such as Assisi, Norcia, and Castelluccio as offering a quieter, more rustic alternative to Tuscany.
Equally popular is Perugia, the regional capital and easily one of the most beautiful cities in Italy. A well-preserved medieval city with a bustling student body supplied by its two universities, compact Perugia is made up of only five neighborhoods (or borgos) holding a population roughly a tenth the size of San Diego.
If you’re only in the city for a short visit, be sure to find a seat on one of the streetside cafes on Corso Vannucci, order an espresso macchiato, and enjoy one of the country’s best people-watching streets.
The Vannucci that gave his name to Perugia’s main drag was a Renaissance artist also known as Perugino. Famous in his own right, Perugino was also Raphael’s teacher, and you can compare the master’s work against the student’s at the impressive Galleria Nazionale Dell’Umbria.
With the rest of your time, settle into the joyous rhythms of Borgo Bello—arguably the city’s most attractive neighborhood—dropping into bars, restaurants, and public gardens with the rolling green hills of Umbria rising up around you.
Florence, the crucible of the Renaissance found about an hour’s drive from Pisa’s Leaning Tower, hardly needs an introduction. The city is an automatic choice for a feature about Italy’s most beautiful cities.
The Tuscan capital is so over-endowed with artistic, architectural, and cultural treasures that the historic center can feel more like a museum than a place where people can actually live. You’ll be transported by the soft sun gleaming off of the Duomo’s pale marble exterior, swoon at Michaelangelo’s immaculate David, and be entranced by Raphael’s Maddalena Doni in the Palatine Gallery.
But what makes Florence more than the sum of its Renaissance parts? The Renaissance came and went but Florence remained, and so did its sense of fashion.
A huge part of the city’s cultural weft, contemporary fashion in Florence is intrinsically tied to the names of Gucci and Ferragamo. Find their museums to see how the stylistic genius of these icons progressed from Tuscan sensations to worldwide stardom.
Read: Two Days in Florence
If you asked an Italian, they’d probably balk at the idea of this grand port city in an article about the most beautiful cities in Italy. While Genoa is the capital of the Italian Riviera, known for picture-perfect destinations such as Portofino, San Remo, and Cinque Terre, Genoa is of a distinctly less dainty disposition than these world-renowned spots.
However, Genoa makes this list for its remarkable interior beauty. With its great wealth accumulated during the medieval period, the former Republic of Genoa splurged on its Rolli Palaces. These 150 UNESCO-listed Renaissance gems, once the property of Genoa’s all-powerful merchant class, are now employed as anything from schools to banks and even public housing (some of the finest examples, however, are maintained as museums).
Annually, over three weekends, the palaces are open to the public, allowing a grand tour of the city’s eye-popping frescos and ornate gilt interiors. It’s a glittering underbelly belied by the otherwise ordinary Italian handsomeness of Genoa.
Of course, this city is also famed for having the largest intact medieval center in Europe (also the same postcode as 42 of the most luxurious Rolli). Whether you find the Centro Storico’s atmospheric flag-stoned alleys and piecemeal piazzas beautiful, however, is something to muse over during a focaccia-heavy Genoese aperitivo.
Siena finds it impossible to avoid comparisons with its larger Tuscan sibling of Florence, so intertwined are the two histories of these former rival republics. That Siena stands up to the comparisons is testimony to its otherworldly charm—the quieter, more intense brother to Florence’s extrovert dandy.
Siena’s tightly wound Gothic streets ramble attractively over a hill in the region’s heartland, about two hours’ drive from Pisa. Children chase down the maze of narrow lanes while cafe seating hopscotches up the steep streets searching for level(ish) perches. As you wander, views over back gardens let in the light, the fragrant herb gardens verdant with the reliable Tuscan sun.
The city suddenly opens up when you enter the reeling Piazza del Campo, home to Siena’s world-famous, fiercely competitive Palio horse race for which the herringbone brick surface is softened with a track of sand. The Gothic architecture reaches its zenith at Siena’s striped 13th-century cathedral, which conceals within its artful gloom the shining Renaissance pearl of the Piccolomini Library.
La Serenissima (or “Most Serene”) has been one of Venice’s official titles since its heyday as an ambitious and powerful medieval republic. Today, this floating city is more likely to be called the “Most Romantic”.
Venice is easily one of the prettiest cities in Italy. The Venetian Gothic architecture applies a delicate lace of stonework to its narrow windows and intimate overwater balconies. The city’s many miles of canal slink along dusky pink and yellow channels, while the illustrious domes of St. Mark’s Basilica float above its namesake square like tethered balloons.
Spend a starlit evening in St. Mark’s sipping chilled Vermentino al fresco while you listen to your restaurant’s string quartet, and you might find yourself googling Italian citizenship.
But La Serenissima’s arsenal consists of more than just its obvious charms. A short vaporetto ride from St. Mark’s Square, the island of Giudecca is quietly transforming itself from an unpromising industrial neighborhood into one of the city’s hot spots for contemporary art. Modernity also has a place in this classical beauty.
The seat of the Savoy royal family, Turin—just under three hours’ drive from Portofino—maintains a quiet dignity and a faded elegance. You’ll find it in the tree-lined boulevards, extravagant palazzos, and the towering backdrop of the snow-capped Alps marking the border with France (best viewed from the top of the city’s symbol, the Mole Antonelliana building).
Make your way swiftly through the city’s industrial extents—Turin is home to Fiat and Alfa Romeo—and into the colonnaded center with its stately avenues. Here you’ll find the spacious urban planning of kings, of ceremony and pomp, with the intention to daunt and dazzle.
Wander the former capital’s idiosyncratic piazzas or pound the marble pavements of boutique-lined Via Roma, recharging with a luxurious bicerin: a regional specialty hot chocolate made with a layer of coffee and another of cream.
The province of Piedmont is, even in Italy, lauded for its cuisine. For a regional trifecta of gastronomic bliss, marry Alba white truffle and rich tajarin egg pasta with a good 20-year-old Barolo. Inhaling violets while soft tannins caress your tongue, muse that perhaps Turin’s quiet dignity is just the sound of a populace with its mouths full.
Under half-an-hour’s drive from Pisa, Lucca is a gem ensconced in the hilly hinterland between Tuscany’s golden coast and the Renaissance kingpin of Florence.
Its historic center encircled by massive—and intact—medieval walls, Lucca was once one of the region’s richest cities. Within this secure stone embrace, the medieval Lucchesi wrought a town plan riddled with snaking alleys and pleasant piazzas shaded by orderly plane trees.
While visiting this Swiss watch of a city, a sense of wellbeing and exclusivity inevitably descends.
Ambiance aside, Lucca’s tangible warren of historic buildings, high-end shops, and timeless cafes makes for a memorable day trip. And that’s only the area below the walls. So accommodatingly wide are the Renaissance-era fortifications that you can hire a bike and do a loop of the town from above. You’ll pass the locals relaxing in the shady parks found on the same elevated level, bulging like billiard-table pockets out of the wall’s line.
Be sure to keep a few euros aside to ascend to the top of the Guinigi Tower. The symbol of Lucca, instantly recognizable for the trees sprouting from its crown, the Guinigi’s balcony offers extraordinary views over Lucca’s intricate urban plan and great angles on the gorgeous Tuscan countryside that surrounds it.
Founded in 734 BC by the Greeks, Syracuse, as seen when approaching across the turquoise Ionian Sea, is a baroque froth of shining limestone rising from the coffee-colored Sicilian earth. From afar, and close up, it’s simply one of the most beautiful cities in Italy and one of the best places to visit in Sicily.
An expert-led tour is the best way to satisfactorily navigate the immense visible history of the Sicilian city’s enchanting interior. Your tour will most likely emphasize how one empire built on the footprint of the last, exemplified by the 7th-century cathedral standing resplendent on the foundations of a Roman temple.
You’ll also see the centers of life in the town, from the sophisticated crescent of the Piazza del Duomo with its sprawling cafe terraces to the morning markets echoing with the shouts of vendors hawking fresh octopus, punnets of glossy red strawberries, and weighty pearls of creamy mozzarella.
Outside of the historic center of Ortigia, treasures such as Latomia del Paradiso await—enchanting gardens set within what were once limestone quarries that helped build the ancient city. Wander amid the sweet scent of the citrus trees mingled with the musky richness of the creeping jasmine. Fathoming the full beauty of this Sicilian city is a multi-sensory journey.
Experience all of these beautiful cities and more on a luxury cruise to Italy. Browse our cruise itineraries online and book an incredible vacation to Italy.