ItalyRome, Vatican, Trevi, Villa d'Este, Florence

Northern Italy is the most economically wealthy and culturally diverse part of the country — where the Alps meet the Mediterranean, where Switzerland and Austria leave their fingerprints on architecture and cuisine, and where some of the finest food, wine, and design in the world is produced. It is also where Italy's three most internationally visited cities outside Rome — Venice, Milan, and Florence — sit within a few hours of each other by high-speed train.

Venice — there is no other city in the world like it, and this is not a cliché but a geographical fact. 118 islands connected by 400 bridges over 150 canals, built on wooden piles driven into the Adriatic mudflats, and inhabited continuously for 1,400 years. Venice has no cars, no traffic noise beyond the sound of water and footsteps, and a quality of light — filtered through sea mist and reflected off canal water — that has attracted painters for centuries for entirely rational reasons. The city is genuinely threatened by acqua alta (flooding) and mass tourism simultaneously, and the tension between these pressures is visible everywhere. Go in November or February; go early or late; get lost in the sestieri beyond San Marco; eat cicchetti at bacaro bars in Dorsoduro. The Frari church, the Scuola Grande di San Rocco, the Accademia — these are where Venice's art history lives most intensely, not the Doge's Palace queue.

Milan — Italy's financial and fashion capital is frequently dismissed as too modern for Italy travel, which is an error. The Duomo (one of the world's largest Gothic cathedrals, and the only one you can walk on the rooftop of) is extraordinary. Leonardo da Vinci's Last Supper, in the refectory of Santa Maria delle Grazie, requires booking months in advance and gives 15 minutes of viewing, which is somehow enough and not enough simultaneously. The Brera neighbourhood — galleries, bookshops, restaurants in a neighbourhood that feels nothing like tourist Italy — is the finest urban afternoon in northern Italy.

The Dolomites — the UNESCO World Heritage mountain range in northeastern Italy is arguably the most photographically extraordinary mountain landscape in Europe. The distinctive vertical pale-limestone peaks — formed from an ancient coral reef and rising directly from green valleys without foothills — are unlike the rounded Alps or the jagged Pyrenees. The Tre Cime di Lavaredo, Val Gardena, and the Alpe di Siusi plateau are the iconic subjects. In summer, the via ferratas (assisted climbing routes on fixed iron rungs) open up the peaks to non-technical climbers. In winter, the Dolomiti Superski area is one of Europe's largest ski networks.

Emilia-Romagna — the region between Bologna and Parma is, by serious culinary argument, the finest food-producing area of Europe. Parmigiano-Reggiano (the real version, aged 24+ months, eaten in chunks with a glass of Lambrusco), Prosciutto di Parma (air-cured ham hung in the ventilated cellars of the Parma hills), aceto balsamico tradizionale di Modena (the real 12–25 year barrel-aged version, nothing like what's sold as balsamic in supermarkets), mortadella, tortellini in brodo, tagliatelle al ragù — the entire canon of Italian food that the rest of the world thinks it understands came from this valley. Bologna's medieval porticoes (40km of covered walkways — a UNESCO site), the food market, and the oldest university in the western world (founded 1088) make it one of the most undervisited cities in Italy.

Central Italy is where the canonical Italian experience lives: Rome's layers of civilisation stacked on top of each other for 2,800 years, Tuscany's cypress-lined roads and Renaissance hill towns, Umbria's truffle markets and medieval walled cities. It is the Italy of the imagination — and it still lives up to it, if you know where to look and when to arrive.

Rome — the city requires at minimum four days to begin to understand, and rewards return visits indefinitely. The classic sites (Colosseum, Roman Forum, Palatine Hill on a combined ticket; the Vatican Museums and Sistine Chapel — book very far in advance; the Pantheon — free, astounding, genuinely worth an hour of silent attention) are justifiably famous. But Rome's deeper character lives in the neighbourhoods: Trastevere's golden-hour alleyways and osterie; the Campo de' Fiori market at 7am; the Gianicolo hill view over the entire city at dusk; the Pigneto district's street art and neighbourhood restaurants where tourists don't go. The aperitivo hour in the Prati district, overlooking the Castel Sant'Angelo as the light goes golden — one of the finest early evenings in Europe.

Florence — the most concentrated museum city on Earth. The Uffizi Gallery alone contains the finest collection of Italian Renaissance painting in the world: Botticelli's Birth of Venus, Raphael, Titian, Caravaggio. The Accademia has Michelangelo's David — the original, which is genuinely different from every reproduction. The Duomo's dome (Brunelleschi's engineering masterpiece, 1436) is best climbed at 8am before the queues. But Florence is also Oltrarno — the neighbourhood south of the Arno, where artisan workshops, wine bars, and restaurants serving Florentine bistecca alla Fiorentina (a T-bone steak of extraordinary size, cooked rare only, over charcoal, served with Chianti) represent a city that has not entirely become a museum of itself.

Tuscany — the landscape that the rest of the world pictures when they imagine Italy. Cypress trees lining white gravel roads (strade bianche) to hilltop farms, vineyards turning golden in October, medieval walled towns above olive groves. Siena's fan-shaped Piazza del Campo (site of the Palio horse race, July 2 and August 16 — a medieval spectacle of extraordinary intensity), San Gimignano's medieval towers, Volterra's alabaster workshops, and the Chianti wine road between Florence and Siena — all within a day's drive. The Val d'Orcia, south of Siena, is the UNESCO landscape most featured in every Tuscany photograph ever taken: rolling hills, solitary farmhouses, and light that arrives at the correct angle in every season.

Umbria — Tuscany's quieter, less visited, deeply Italian neighbour. Assisi (birthplace of St Francis, its basilica with Giotto frescoes on a hillside above olive groves), Orvieto (a cathedral whose facade of golden mosaics is one of the finest Gothic architectural surfaces in Italy), Spoleto, and Norcia (the capital of Italian black truffle and the place where the best porchetta and salumi in the country is produced) compose a region that rewards slow travel and rewards those who come in spring and autumn when the hill towns are at their most themselves.

Southern Italy is the Italy that Italians from the north have historically dismissed and foreigners have increasingly discovered. It is louder, sunnier, more chaotic, more generous, and — in the judgement of most people who travel there — more genuinely Italian than the polished tourism infrastructure of the north. The food is bolder, the welcome is warmer, and the historical layers are, if anything, denser.

Naples — the most misunderstood major city in Italy and, for those who understand it, one of the most extraordinary. Built on the slope of an active supervolcano (the Campi Flegrei caldera, not just Vesuvius), with 3,000 years of continuous habitation, a UNESCO historic centre of extraordinary density, and a street food culture of unmatched quality. The pizza here is a UNESCO Intangible Cultural Heritage — the Neapolitan Pizzaiuolo tradition, the technique of wood-fired baking at 485°C that produces a crust simultaneously charred and pillowy with edges that bubble and blister. Eat it at Brandi (which claims to have invented the Margherita in 1889) or at one of the street windows in the Quartieri Spagnoli. Below Naples: the archaeological sites of Pompeii and Herculaneum (both reachable by the Circumvesuviana train), where Vesuvius's 79 CE eruption preserved Roman daily life with an intimacy that no other site in the world provides.

The Amalfi Coast — the 50km coastal road from Positano to Salerno is one of the most dramatic drives in Europe and one of the most crowded in summer. The clifftop towns of Positano, Ravello (with its hillside gardens overlooking the sea, where Wagner composed parts of Parsifal), and Amalfi itself offer the canonical Mediterranean experience at peak tourist intensity. Visit in May or October for the combination of open businesses and manageable crowds. Capri (accessible by ferry from Naples or Sorrento) rewards those who stay overnight after the day-trippers leave.

Puglia — Italy's most compelling region right now, and the one least remade for tourism. The heel of Italy's boot: trulli (unique conical stone houses, UNESCO-listed, concentrated around Alberobello), the Baroque city of Lecce (whose ornate facade carvings in soft local limestone are so exuberant that the style is called "Barocco leccese"), Ostuni's white city on a hill, the Gargano peninsula's sea caves, and the best mozzarella and burrata in the world (fresh, made that morning, eaten at the source). The food is anchored in olive oil — Puglia produces 40% of Italy's olive oil — with orecchiette pasta (ear-shaped, made by hand on street corners in Bari Vecchia), raw seafood, and a directness of flavour that makes northern Italian cooking look timid.

Sicily — an island with its own history that is simultaneously Italian and entirely not. The largest island in the Mediterranean, a crossroads of Phoenician, Greek, Roman, Arab, Norman, Spanish, and Italian civilisations, each of which left visible architecture. The Greek temples at Agrigento (Valley of the Temples — five temples in a row, some of the best-preserved Greek structures outside Greece, on a ridge above almond blossom in February) and the Theatre of Syracuse, where Aeschylus premiered tragedies and the performances continue in May. Mount Etna — Europe's most active volcano, 3,329 metres, snow-capped for much of the year, visibly smoking — is climbable with a guide from Catania or Taormina. The street food of Palermo (panelle, arancini, pani ca meusa — a spleen sandwich of legendary intensity) is among the finest in Italy.