Choosing where to go in Italy is genuinely one of the most overwhelming travel decisions you’ll ever make — and I say that as a compliment to the country.
It’s not that the choices are difficult because some of them are bad. They’re all good. Every single one. The problem is that Italy is almost unfairly stacked with incredible cities, and no matter how carefully you plan your itinerary, you’re going to leave knowing you missed something amazing. That’s just the Italy experience.
Your colleague swears by Rome and says nothing else comes close. Your neighbour spent a week in Sicily and won’t shut up about it. The travel blog you’ve been following for three years posts exclusively about Puglia and makes it look like the most beautiful place on earth. And they’re all right.
I’ve travelled Italy enough times now to know that the best approach isn’t trying to find the “right” answer — it’s figuring out what kind of trip you actually want, and then building from there. So here’s a list of 16 cities that covers every kind of Italy: the iconic, the underrated, the foodie obsession, the history lesson, and the ones that quietly rearrange your priorities without you even realising.
Grab an espresso. Let’s get into it.
1. Bologna — The Foodie Capital Italy Doesn’t Talk About Enough
If there is one city in Italy that is criminally underrated in travel conversations, it’s Bologna. And if food is anywhere on your list of priorities — which, if you’re going to Italy, it absolutely should be — then Bologna might just be the best city in the entire country to visit.
Bologna sits comfortably in the Emilia-Romagna region of northern Italy, right in the heart of the Po Valley, and this region produces some of the most celebrated food in all of Europe. Parmigiano Reggiano, Prosciutto di Parma, mortadella, fresh egg pasta, ragù alla bolognese — yes, the real one, not what the rest of the world calls “bolognese” — all come from here. The food in Bologna isn’t just good, it’s foundational. It’s why Italian food is what it is.
But Bologna isn’t only about eating, as wonderful as that sounds. The city itself is beautiful in a slightly understated way — all warm terracotta buildings and long arcaded walkways called portici that run for miles through the streets, keeping you sheltered from sun and rain alike. The UNESCO-listed porticoes of Bologna are one of the most distinctive architectural features in any Italian city, and walking under them through the old town feels genuinely special.
Start your visit at Piazza Maggiore, the main city square, which is everything a great Italian piazza should be — grand but liveable, busy but not hectic. The Neptune Fountain at the edge of the square is a gorgeous piece of Renaissance sculpture that the Bolognese have completely normalised as a backdrop for their daily coffee run. Take a moment to appreciate it before you do the same.
Right off the square, the Basilica of San Petronio is enormous — and I mean that in the most literal sense. It’s one of the largest churches in the world by volume, and the unfinished brick facade somehow makes it even more dramatic than a polished one would. Step inside and the scale hits you immediately.
For food (and you absolutely cannot leave without eating properly here), track down a Tagliere — one of those simple, generous boards of local cold meats, regional cheeses and whatever else the kitchen fancies — and pair it with a glass of local Pignoletto. Or go straight to dessert and order a Zuppa Inglese, a rich, layered dessert somewhere between a trifle and a tiramisu that’s entirely Bologna. For the best version of it, head to Trattoria di Via Serra and consider it non-negotiable.
Don’t miss: Piazza Maggiore, the Neptune Fountain, Basilica of San Petronio, the Two Towers, the Quadrilatero food market, and the porticoes at golden hour.
2. Matera — The Ancient Cave City That Will Completely Stop You in Your Tracks
There are cities you visit and think, “yes, this is very nice.” And then there’s Matera, which stops you completely the moment you set eyes on it and takes a few seconds to fully process.
Matera is one of the oldest continuously inhabited cities in the world — people have been living here for roughly 9,000 years, which means this city was already ancient when the Roman Empire was getting started. It sits in the southern Basilicata region, carved into and around a deep ravine in the landscape, and the effect is unlike anything else in Italy or, frankly, anywhere.
The heart of it all is the Sassi di Matera — a vast complex of cave dwellings, churches, and houses literally carved into the ravine walls and the rock face below. People lived in these caves from prehistoric times right up until the 1950s, when the government relocated the residents to modern housing because the conditions were considered too poor. For decades the Sassi were seen as an embarrassment, a symbol of southern poverty. Then UNESCO gave the whole area World Heritage Status in 1993, and the world slowly began to realise what Matera actually was: one of the most extraordinary places in Europe.
Walking through the Sassi now is a surreal experience. Narrow stone paths wind between ancient dwellings, cave churches (called rupestrian churches) hide behind unassuming doors, and panoramic viewpoints open up over the ravine to reveal just how vast and complex the whole system really is. At night, when the cave city is lit up and glowing against the dark ravine, it’s one of the most cinematic sights in Italy. Matera was named a European Capital of Culture in 2019, and the world finally caught up.
For dinner, try to get a table at Dedalo — a restaurant built inside a cave (the whole city feels like this is normal, and somehow it is) that serves exceptional southern Italian food. The setting alone is worth it, but the food actually delivers. If you really want to go all in, Aquatio Cave Hotel has rooms carved directly into the ancient rock with views over the ravine and an extraordinary cave pool. Staying there is the kind of experience you’ll be describing to people for years.
Don’t miss: The Sassi di Matera at sunrise and sunset (both are extraordinary), the rupestrian cave churches, the panoramic viewpoint at Piazza Pascoli, a cave dinner, and the Matera Cathedral sitting high above the ravine.
3. Florence — The City That Invented the Renaissance (And It Shows)
Florence is, for a lot of people, the city that makes Italy feel like Italy.
It’s not the largest city on this list, and it’s not the loudest or the most chaotic. But Florence has a quiet confidence about it — the kind of city that doesn’t need to shout because the evidence of its greatness is everywhere you look, built into every church facade, every gallery, every palazzo and every bridge over the Arno River.
This is where the Renaissance began. Not metaphorically — literally. The Medici family, arguably the most influential patrons in the history of art, lived and ruled from here, and they spent their considerable wealth commissioning the greatest artists of the age: Botticelli, Michelangelo, Leonardo da Vinci, Brunelleschi. The result is a city that is essentially one enormous open-air museum, and it doesn’t feel artificial or preserved for tourists — it just feels like Florence.
The Uffizi Gallery is the obvious starting point if art is your reason for being here, and if art is anywhere in your interests at all, make it your reason. This is one of the greatest art museums in the world, housing work from Botticelli, Raphael, Titian, Caravaggio and dozens of other masters across room after gorgeous room. You could spend a full day here and still feel like you’ve only scratched the surface. Book tickets in advance — the queues without a reservation are brutal.
The Florence Cathedral (Santa Maria del Fiore) and Brunelleschi’s famous dome are one of those rare sights that look even better in person than in any photo you’ve ever seen. The dome itself was an engineering impossibility when Brunelleschi proposed building it, and somehow he built it anyway. Climb to the top if you have the legs for it — the view over Florence’s rooftops and terracotta is one of the great city views in Europe.
Ponte Vecchio, the medieval bridge lined with jewellery shops that spans the Arno, is exactly as charming as everyone says — try to be there early in the morning before the crowds arrive, or at dusk when the light hits the water and the whole bridge seems to glow.
For the best free view in Florence, make the 25-minute uphill walk to Piazzale Michelangelo. The panorama over the city at golden hour, with the Duomo dominating the skyline, is completely free and completely unforgettable. Bring a bottle of local wine, find a spot on the steps, and just sit with it for a while. For dinner, Buca Mario is one of the oldest restaurants in Florence and serves a Florentine steak (bistecca alla Fiorentina) that is genuinely enormous. You’ve been warned.
Don’t miss: The Uffizi Gallery, the Duomo and Brunelleschi’s dome, Ponte Vecchio, Piazzale Michelangelo at sunset, the Boboli Gardens, and the Oltrarno neighbourhood for a more local feel.
4. Ragusa — Sicily’s Baroque Jewel That Most Tourists Miss
If there’s a city on this list that rewards visiting precisely because it hasn’t been overrun yet, it’s Ragusa.
Perched dramatically in the hilly interior of southern Sicily, Ragusa is a UNESCO World Heritage Site and one of the eight Val di Noto Baroque towns that were rebuilt from scratch after a catastrophic earthquake in 1693 flattened the region. The towns that rose from that destruction were rebuilt in an extraordinary, theatrical Baroque style, and Ragusa is arguably the most beautiful of them all.
People have been living in this area for over 4,000 years — it’s one of the oldest continuously occupied sites in Sicily — and you feel that depth of history in every stone. The city is split into two distinct parts: the newer upper city and the older Ragusa Ibla in the lower section, which is where all the most beautiful architecture is concentrated and where you’ll want to spend the majority of your time.
Wander through the narrow streets of Ibla and you’ll find gorgeous Baroque churches, quiet piazzas, ornate stone balconies dripping with wrought iron, and a pace of life that feels genuinely unhurried. The Duomo di San Giorgio is the centrepiece of the whole area — a soaring Baroque masterpiece with an extraordinary facade that dominates the main piazza and is, by any measure, one of the finest churches in Sicily.
For food, Ristorante Duomo in Ragusa Ibla has a Michelin star and is widely considered one of the best restaurants in Sicily. The cooking is rooted in deep Sicilian tradition but elevated with real care and creativity — if you’re going to splash out on one special dinner in Sicily, this might be where you do it. Stay in the old town if you can, ideally somewhere with views over the surrounding valley — waking up inside Ibla is a fundamentally different experience from staying outside the historic centre.
Don’t miss: Ragusa Ibla, the Duomo di San Giorgio, the Baroque balconies and facades along Corso XXV Aprile, the views from the Ibla gardens, and day trips to the nearby Val di Noto towns of Noto and Modica.
5. Bergamo — The Fortified City Just Outside Milan That Everyone Should Visit
Bergamo is the city I recommend to people who say they’ve “done Milan and want something different” — and it never fails to deliver.
Located about 50 minutes northeast of Milan, Bergamo is often treated as a quick day trip or an airport city (Bergamo Orio al Serio handles a lot of Milan’s budget flight traffic). That’s a category error. Bergamo is a proper, fascinating, beautiful city in its own right, and the people who treat it as a footnote to Milan are genuinely missing something.
The city divides into two very distinct parts: the modern lower city, which is pleasant enough, and the Città Alta (upper city), which is something else entirely. The Città Alta sits on a hill enclosed by 16th-century Venetian walls — walls that are so impressive they’ve been granted UNESCO World Heritage Status in their own right — and the whole area within them feels like a preserved piece of medieval northern Italy. Take the funicular up from the lower city and the transformation is immediate.
Piazza Vecchia at the heart of the upper city is one of the most beautiful squares in Lombardy, surrounded by arcaded buildings, a medieval tower, and the Biblioteca Civica (a gorgeous old library). The Basilica di Santa Maria Maggiore just off the square is extraordinary inside — covered floor to ceiling in intricate tapestries, carved wood and gilded decoration that’s almost overwhelming. The views out over the surrounding Lombardy countryside from the upper city walls are genuinely lovely, especially in the late afternoon.
Bergamo also has a fantastic food scene — it’s big on polenta, local cheeses and cold meats, and the casoncelli pasta (filled with a sweet and savoury meat mixture) is a local speciality worth hunting down. The city has a relaxed, real atmosphere that the bigger tourist destinations can lose. Spend an evening here and you’ll understand what I mean.
Don’t miss: The Città Alta and its Venetian walls, Piazza Vecchia, Basilica di Santa Maria Maggiore, the funicular, the view from the upper city, and the local casoncelli pasta.
6. Perugia — Umbria’s Hilltop Gem Right Between Florence and Rome
Most people travelling between Florence and Rome choose to take the fast train and skip everything in between. Perugia is one of the better arguments for slowing down.
The capital of Umbria sits on a hilltop with long views over the surrounding green valley, and it’s a city that has far more going on than its size would suggest. It’s got a beautiful medieval old town, a good arts scene, a chocolate festival that people travel from across Italy to attend (the annual Eurochocolate festival in October is genuinely enormous), and the kind of authentic local character that cities on the main tourist trail often lose.
Piazza IV Novembre is the heart of the old city and one of the finest medieval squares in Italy — anchored by the magnificent Fontana Maggiore, a 13th-century fountain decorated with detailed sculptural panels that is still considered a masterpiece of medieval art. The Palazzo dei Priori on the same square houses the impressive National Gallery of Umbria, which has an excellent collection of Umbrian painting and is far less visited than the famous galleries in Florence and Rome.
The Rocca Paolina is a 16th-century fortress that was built by Pope Paul III and is now partially accessible underground — you can walk through a subterranean layer of the old medieval city that was buried beneath it, which is one of those unexpected experiences that makes travel genuinely surprising.
For food and wine in a proper local setting, Vineria La Fraschetta on Via Antonio Gramsci is exactly the kind of restaurant you hope to stumble onto: small, unpretentious, great home cooking, generous pours and an atmosphere that makes you want to stay for hours. Perugia is also excellent for day trips — Assisi is only about 25 minutes away, and the hill towns of Umbria are all within easy reach.
Don’t miss: Piazza IV Novembre, the Fontana Maggiore, the Palazzo dei Priori, the underground Rocca Paolina, and the views over the Umbrian valley from the old town walls.
7. Milan — More Than Fashion, More Than Finance
Milan is the Italian city that gets the most unfair treatment in travel writing. Too many people spend a single day there, walk around the Duomo and the Galleria, decide it’s “not really their Italy,” and leave. Those people haven’t seen Milan.
Yes, Milan is Italy’s fashion capital and its financial engine. Yes, it has a sleeker, more corporate energy than Rome or Naples. But it’s also home to some of the most extraordinary art, architecture and food in the country — and once you get past the surface impression, it opens up into something genuinely brilliant.
Leonardo da Vinci’s The Last Supper is at the top of any Milan itinerary for good reason. Housed in the refectory of the church of Santa Maria delle Grazie, it’s one of the most celebrated paintings in human history, and seeing it in person — in the room it was made for, at the scale it was painted — is genuinely moving. Book tickets weeks in advance. They are strictly limited and they sell out completely. Don’t show up without a reservation and expect to get in.
The Milan Cathedral (Duomo di Milano) is spectacular in a way that takes your breath away even if you’ve already seen a hundred European cathedrals. It’s the world’s largest Gothic cathedral, took nearly six centuries to complete, and the rooftop — which you can walk along — gives you an extraordinary close-up view of the hundreds of spires and statues while the city spreads out below you. Go up at dusk if you can.
Right next to the cathedral, the Galleria Vittorio Emanuele II is one of the most beautiful covered shopping arcades in the world — even if you’re not buying anything, walking through the glass-vaulted galleria with its mosaic floors and operatic architecture is one of the great small pleasures of any Italy trip.
And if you have an extra day (or even half a day), Lake Como is just 50 minutes north. The train ride up is beautiful, the lake itself is genuinely one of the most stunning places in northern Italy, and the lakeside towns of Varenna and Bellagio are the kind of places that make you understand why people fall in love with this country so easily.
Don’t miss: The Last Supper (book ahead!), the Duomo and its rooftop, Galleria Vittorio Emanuele II, the Brera neighbourhood for art and aperitivo, the Navigli canals at sunset, and Lake Como for a day trip.
8. Mantua — The Renaissance Gem Sitting Quietly Between Three Lakes
Mantua is one of those cities that I feel genuinely guilty about not visiting sooner, and one that I now recommend to anyone who tells me they’ve already done the Italian classics and want something different.
Located in Lombardy, southwest of Verona and surrounded on three sides by lakes formed by the Mincio River, Mantua was once one of the great cultural centres of the Italian Renaissance. The Gonzaga family ruled here for centuries and spent their considerable power and wealth accumulating art, commissioning architecture and turning Mantua into a city of extraordinary sophistication. Walking around it today, that legacy is completely tangible.
The Ducal Palace (Palazzo Ducale) is vast — over 500 rooms spread across multiple buildings — and includes the famous Camera degli Sposi, a small room painted entirely by Andrea Mantegna with one of the most extraordinary illusionistic ceiling decorations in Renaissance art. The Palazzo Te on the edge of the city is another Gonzaga masterpiece: a summer pleasure palace decorated with stunning frescos, including the spectacular Room of the Giants where the entire room is painted to look like the walls are collapsing. It’s theatrical and magnificent and unlike anything else.
Mantua’s historic centre is compact and easy to walk, with beautiful piazzas, a lovely cathedral, and a lakeside atmosphere that makes the whole city feel pleasantly unhurried. For a quick, local lunch, La Piadineria is the place to track down proper piadine — the flatbread wraps filled with local cheeses, meats and vegetables that are a staple of this part of Italy. Simple, excellent, very Mantua.
Don’t miss: The Ducal Palace and Camera degli Sposi, Palazzo Te, Piazza Sordello, the lakeside promenade, and the view of the city from the lake at dusk.
9. Naples — Chaotic, Brilliant, and Home to the World’s Best Pizza
Naples has a reputation that precedes it, and that reputation keeps a lot of travellers away. Those travellers are missing one of the most electrifying cities in Italy.
Yes, Naples is chaotic. The traffic is genuinely lawless. The streets in the old town are narrow and dark and occasionally overwhelming. It is loud and intense and the pace of everything here is pitched slightly higher than anywhere else in Italy. And it is, for exactly those reasons, one of the most alive cities you’ll ever visit.
Naples doesn’t perform for tourists. It doesn’t try to look polished or curated. What you see is what it actually is — a dense, loud, passionate, brilliant city that has been continuously inhabited for over 2,800 years and isn’t particularly interested in smoothing off its rough edges for anyone. That authenticity, in a world of increasingly similar tourist experiences, is genuinely refreshing.
And then there’s the food. Neapolitan pizza, made properly with San Marzano tomatoes grown on the volcanic slopes of Vesuvius, fior di latte mozzarella and a proper wood-fired crust, is in a completely different category from anything else you’ve eaten that shares the name. Head to Sorbillo or Di Matteo on Via dei Tribunali — locals queue outside both, which tells you everything you need to know. Eat standing at the counter if there’s no table. Don’t overthink the topping.
Beyond pizza, the National Archaeological Museum (Museo Archeologico Nazionale) houses the largest and most important collection of ancient Roman artefacts in the world, much of it rescued from Pompeii and Herculaneum. The mosaics alone are worth the visit. The Catacombe di San Gennaro are eerie, fascinating and surprisingly moving. And the Teatro di San Carlo — Italy’s oldest opera house, opened in 1737 — is one of the most beautiful theatre interiors in Europe.
Use Naples as your base and make the 30-minute train journey to Pompeii — it’s one of the most extraordinary historical sites on earth and best experienced in a separate, dedicated visit rather than crammed into a day trip from Rome.
Don’t miss: Pizza on Via dei Tribunali, the National Archaeological Museum, the Spaccanapoli street running through the old town, Castel dell’Ovo for sunset, and Pompeii as a day trip.
10. Pompeii — Walking Through a Moment Frozen in Time
Pompeii is unlike any other historical site in Italy — or, honestly, in the world.
In 79 AD, Mount Vesuvius erupted and buried the thriving Roman city of Pompeii under meters of volcanic ash in a matter of hours. The ash preserved everything: streets, buildings, homes, bakeries, bathhouses, wine shops, election notices painted on walls, and the people themselves — captured in their final moments as plaster casts that remain one of the most haunting and unforgettable things you’ll see anywhere.
Walking through the ancient streets of Pompeii is one of those travel experiences that genuinely changes your relationship with history. This isn’t a museum reconstruction — it’s the actual city, preserved as it was on the day it died. You walk on the original Roman paving stones, peer into the actual rooms where people cooked and slept and traded, and read graffiti left by people 2,000 years ago. The sense of proximity to another time is extraordinary.
The site is large — properly large — and a full visit takes at least three to four hours. The Forum, the Amphitheatre, the Lupanar (brothel, with its remarkable wall paintings), the Villa of the Mysteries and the Garden of the Fugitives (where the plaster casts of victims are displayed in situ) are all essential stops.
One piece of practical advice: arrive early. The site opens at 9am and the first hour or so is significantly less crowded than midday. Getting there 20 minutes before opening and heading straight to the far end of the site before doubling back means you’ll have entire sections almost to yourself before the tour groups arrive.
Don’t miss: The Forum, the Amphitheatre, the Villa of the Mysteries, the Garden of the Fugitives, and the view back toward Vesuvius from the site — knowing what that mountain did makes looking at it rather different.
11. Rome — The Eternal City That Lives Up to Every Single Thing Said About It
Rome was always going to be on this list. There is genuinely no getting around it, and there’s no good reason to try.
The city has been continuously inhabited for nearly 3,000 years, was the centre of one of history’s greatest empires, gave the Western world its legal foundations, its alphabet, its road network and a considerable chunk of its architecture — and the evidence of all of that is simply everywhere you look. In any other city, the Colosseum would be the undisputed centrepiece of everything. In Rome, it’s competing with the Pantheon, the Trevi Fountain, the Roman Forum, the Borghese Gallery and the entire sovereign city-state of Vatican City for your attention. Rome is almost unfairly loaded.
But the thing about Rome that hits you when you actually spend time here is that it’s not just a collection of monuments — it’s a functioning, breathing, incredibly lived-in city that happens to contain an almost incomprehensible amount of history. The cafés are full of people having the same conversations they would in any city. The morning markets are selling the same vegetables they’ve been selling in these piazzas for centuries. Rome absorbs history into daily life in a way that is completely unique.
For something slightly off the main tourist circuit, wander into the Campo de’ Fiori morning market and grab a piece of Pizza Bianca from Forno di Campo de’ Fiori — one of Rome’s oldest bakeries, which has been making it for over 500 years. Then just walk. Get away from the big landmarks and lose yourself in the streets around the Trastevere neighbourhood as the evening begins — ivy-covered walls, the smell of cooking coming from every door, cobblestones slick from an afternoon rain, restaurants filling up with locals who eat late and linger even later. That’s Rome at its most magical.
Don’t miss: The Colosseum and Roman Forum (book ahead), the Pantheon, Vatican City and the Sistine Chapel (book very far ahead), the Trevi Fountain at dawn before crowds arrive, the Borghese Gallery, and Trastevere for dinner.
12. Siena — The Medieval Rival to Florence That Has Never Stopped Being Magnificent
Siena and Florence spent centuries as bitter rivals — competing commercially, militarily and artistically. Florence eventually won. But Siena, frozen in its medieval glory as a result, is now one of the most beautiful and best-preserved medieval cities in Italy, and arguably more immediately lovely than its old rival.
The Piazza del Campo is the heart of Siena and one of the greatest public spaces in Europe — a sweeping, fan-shaped piazza built on a natural slope, ringed by medieval palaces and completely free of cars. Sitting here with an Aperol Spritz watching Sienese life carry on around you is one of the great Italian afternoon experiences. The piazza is also where the famous Palio di Siena takes place — a bareback horse race around the square that has been run twice yearly since the 13th century and which turns the whole city into an extraordinary spectacle of medieval pageantry. If your visit lines up with it (July 2nd or August 16th), don’t miss it for anything.
The Siena Cathedral (Duomo di Siena) is jaw-dropping both inside and out. The striped marble facade is dazzling; the interior is even more extraordinary, with a spectacular inlaid marble floor, a Nicola Pisano pulpit that is one of the masterpieces of medieval sculpture, and a stunning library (the Piccolomini Library) painted with vivid frescos by Pinturicchio. Climb the Torre del Mangia — 14th century, 85 metres tall, 505 steps — for one of the best views in all of Tuscany.
For dinner, La Taverna di San Giuseppe is excellent — proper Sienese cooking, an outstanding wine cellar built into the medieval rock below the restaurant, and the kind of atmosphere that makes a three-hour dinner feel entirely justified. Make a reservation; it’s consistently full.
Don’t miss: Piazza del Campo, the Duomo and its library, Torre del Mangia, the Pinacoteca Nazionale, and the city walls for a walk with valley views.
13. Turin — Italy’s Most Underrated City, and I’ll Argue That With Anyone
If you mention Turin in a group travel conversation, at least one person will say, “Oh, is that worth visiting?” Yes. Emphatically yes. And if Italy keeps producing lists that relegate Turin to footnote status, we need to fix that.
Turin was Italy’s first capital city after unification. It’s the birthplace of Fiat, of the Slow Food movement, and of quite a few things you eat and drink regularly without knowing their Italian origins. It has wide, Parisian-style boulevards, beautiful arcaded streets, excellent coffee, and a food culture that takes itself very seriously — in exactly the right way.
The Mole Antonelliana is Turin’s defining landmark — a soaring, needle-like building originally designed as a synagogue and now home to the National Museum of Cinema, one of the most creative and brilliantly designed museums in Italy. The building itself has a glass elevator running up through its interior to a viewing platform with panoramic views over Turin and the Alps beyond. Take it.
The Egyptian Museum (Museo Egizio) in Turin is the second most important collection of ancient Egyptian artefacts in the world after Cairo — which is a sentence that surprises most people who hear it. It’s extraordinary, and if you have any interest in ancient history, it’s essential.
The Mole Cathedral is home to the Shroud of Turin — the linen cloth that some believe was the burial shroud of Jesus Christ, and which has been debated, tested and studied for centuries without a definitive conclusion. Whatever your view on its authenticity, the shroud and the story surrounding it are genuinely fascinating.
For food, Casa Vicina does exceptional Piedmontese cooking with a wine list that reflects just how seriously this region takes its wine — and Piedmont wine, including Barolo and Barbaresco, is among the greatest in Italy. Before you leave Turin, find a café serving a Bicerin — espresso layered with hot chocolate and thick cream, invented right here in the city and completely unlike anything you’ve had before. It’s one of those small, perfect things that travel delivers.
Don’t miss: The Mole Antonelliana and Cinema Museum, the Egyptian Museum, Piazza Castello, the Palazzo Reale, the arcaded streets of the city centre, and a Bicerin at Caffè Al Bicerin where it was invented.
14. Venice — The City That Shouldn’t Exist But Absolutely Does
There is nowhere in the world like Venice. That isn’t marketing language or hyperbole — it is simply the factual truth.
Venice was built across 118 small islands in a lagoon in the northeastern corner of Italy, connected by over 400 bridges, with canals running where other cities have roads and boats floating where other cities have taxis. It shouldn’t work. It shouldn’t have lasted. And yet here it is, still standing, still functioning, still one of the most beautiful and singular places human beings have ever built, well over 1,000 years after its founding.
St. Mark’s Basilica and the surrounding Piazza San Marco are breathtaking — the basilica’s Byzantine mosaics, its golden interior and its improbable blend of architectural styles from centuries of Venetian conquest make it unlike any other cathedral in Italy. The Doge’s Palace next door tells the story of the Venetian Republic, and the Bridge of Sighs connecting them carries one of history’s more poetic legends. The Peggy Guggenheim Collection on the Grand Canal is one of the finest collections of modern art in Europe, housed in a stunning white palazzo right on the water.
But the most important Venice advice I can give anyone is this: leave the tourist areas. Walk away from the Rialto and San Marco and get deliberately, entirely lost in the quieter sestieri — the Dorsoduro, the Cannaregio, the Castello. You will lose your bearings completely. You will make wrong turns constantly. That is the point. Venice only reveals itself in its quieter streets, at the end of a narrow alley that opens suddenly onto a deserted canal with a single gondola passing in the green water below. That moment — repeated over and over — is the real city.
For dinner, Osteria Boccadoro serves creative, thoughtful Venetian food built around the freshest fish and seafood from the market. The menu changes constantly. It’s always worth it. Take the vaporetto to Murano for the glassblowing workshops, and to the wildly colourful island of Burano for arguably the most photogenic streets in all of Italy. Both are completely worth the boat trip.
Don’t miss: St. Mark’s Basilica and Square, the Doge’s Palace, the Peggy Guggenheim Collection, a vaporetto ride down the Grand Canal, the quiet streets of Dorsoduro at night, Murano, and Burano.
15. Verona — Shakespeare Set a Love Story Here, and It’s Easy to See Why
Verona gets reduced to a Romeo and Juliet reference in most travel writing, which is both understandable and deeply unfair to a city that is genuinely magnificent on its own considerable merits.
Yes, Juliet’s House is here, and yes, there’s a courtyard with a bronze statue and a balcony and thousands of love notes stuck to the wall — it’s charming in a slightly absurd way and absolutely worth five minutes of your time. But Verona is so much more than one piece of literary tourism.
The Arena di Verona is one of the largest and best-preserved Roman amphitheatres in the world, built in the 1st century AD and still in active use today. Every summer, it hosts a season of open-air opera — Aida, Carmen, Nabucco — performed in a 2,000-year-old stadium under the Italian stars. If your visit aligns with the opera season (June through September), an evening at the Arena is one of the most extraordinary live experiences in Europe, full stop. The tickets aren’t cheap, but they’re not wildly expensive either, and the experience is absolutely priceless.
Beyond the Arena, Castelvecchio — a 14th-century castle on the Adige River, now a beautifully converted museum with an excellent art collection — is one of the great lesser-known museum experiences in northern Italy. The view from the medieval bridge attached to it is stunning. And the sunset from Piazzale Castel San Pietro on the hill above the city, looking down over the red rooftops and the arc of the Adige River winding through the centre, is one of the very best evening views in northern Italy.
Don’t miss: The Arena di Verona (opera season if possible), Piazza delle Erbe, Castelvecchio, Piazzale Castel San Pietro for sunset, the Adige riverfront, and the Romanesque Basilica di San Zeno.
16. Bari — Your Gateway to the Real Southern Italy
Bari is the kind of city that rewards arriving with absolutely no expectations — because it will exceed them in ways you didn’t anticipate.
The capital of Puglia sits on the Adriatic coast in the heel of Italy’s boot, and it’s a city that most people use purely as a transit hub for the wider region. That’s a mistake. Bari itself is brilliant, particularly the ancient old town — Bari Vecchia — which is one of the most authentic and characterful historic centres in all of southern Italy.
Bari Vecchia is a tightly packed labyrinth of narrow streets where you can still find local women sitting in their doorways every morning, making orecchiette pasta by hand and selling it fresh right there on the street. This is not a tourist performance or a reconstruction — it’s just what they do, what their mothers did, what their grandmothers did before that. Watching it happen, buying a bag and walking away, is one of those simple travel moments that sticks with you.
The Basilica di San Nicola is a major pilgrimage site with beautiful Romanesque architecture — San Nicola (St. Nicholas, the historical basis for Santa Claus) is buried here, which gives the basilica a quiet but palpable spiritual significance that makes visiting it feel different from a standard church visit. The Bari Cathedral (Cattedrale di San Sabino) next to it is equally beautiful and far less visited.
The seafront promenade (Lungomare) is perfect for an evening walk — the Adriatic stretches away to the east and the city lights up beautifully at dusk. The newer Murat quarter has excellent restaurants, buzzing bars and a genuine local energy that makes it a wonderful place to spend an evening.
And Bari is your launchpad for the rest of Puglia — the beehive-shaped trulli houses of Alberobello, the beautiful white city of Lecce (often called the Florence of the South for its extraordinary Baroque architecture), the sea caves of Polignano a Mare, and some of the finest burrata, fresh pasta and seafood you’ll eat anywhere in the world.
Don’t miss: Bari Vecchia and the orecchiette makers, Basilica di San Nicola, the Lungomare promenade, Polignano a Mare as a day trip, Alberobello’s trulli, and fresh burrata at every possible opportunity.
Final Thoughts — Italy Rewards the Curious Traveller
The thing about Italy is that the obvious cities — Rome, Florence, Venice — are obvious for very good reasons and they absolutely live up to their reputations. Go to them, especially if it’s your first time. They’ll deliver everything they promise.
But Italy also has a whole other layer underneath the headline acts, and that’s where some of the most memorable travel moments happen. A late-night plate of fresh pasta in a Naples side street. Standing inside the Sassi of Matera and trying to comprehend 9,000 years of continuous human habitation. Getting completely lost in Venice’s back canals at sunset and not caring even slightly.
My honest advice: mix the classics with one or two cities you wouldn’t normally book. Leave room for wandering. Eat everything. Be open to the unexpected. And maybe — just maybe — consider skipping the fast train between the big cities and stopping somewhere in the middle that you’ve never thought about before.
Italy rewards the curious. That’s always been true. And given how much beauty this country is hiding in plain sight, it will stay true for as long as people keep showing up with open eyes.
