A first-timer's guide to Italy

Everything a first trip needs and nothing it doesn't — how to choose where to go, when to visit, what it costs, and the handful of local rules that make the difference.

By The Pilot

The first trip to Italy almost always follows the same golden path: Rome, Florence, Venice, maybe a day on the Amalfi Coast. It’s a wonderful introduction — and then it quietly spoils you, because the second trip is where Italy really opens up. With the headline cities behind you, you can pick a single region most visitors skip and give it a whole week. Here are six worth building a trip around, each a country unto itself.

Piedmont — for food, wine and quiet grandeur

Tucked under the Alps in the north-west, Piedmont is Italy at its most refined and least crowded. This is the land of Barolo and Barbaresco, of white truffles shaved over egg pasta in autumn, of elegant Turin with its arcaded avenues and café culture. The rolling Langhe vineyards feel like Tuscany before the tour buses found it. Come in autumn for the harvest and the truffle fairs.

Puglia — the sun-baked heel

Down in the far south-east, Puglia is all whitewashed towns, olive groves, and a long coastline of clear water. Its signature sight is Alberobello, a town of trulli — conical stone huts that look like something from a fairy tale — but the real pleasure is slower: seafood on the harbour, the baroque honey-coloured stone of Lecce, and beaches that rival anywhere in the Mediterranean without the price tag. It’s hot, easy and joyful.

Sicily — a whole world on one island

Sicily isn’t a region so much as a crossroads with three thousand years of history layered into it — Greek temples better preserved than any in Greece, Norman cathedrals, Arab-influenced street food, and Mount Etna smoking over it all. The food alone justifies the trip: arancini, cannoli, granita for breakfast, and the freshest fish you’ll eat anywhere. Give it more time than you think you need; it’s bigger and richer than it looks.

The Dolomites — Italy goes vertical

Up in the far north-east, the landscape and even the language change: this is a German-and-Italian-speaking world of jagged pale peaks, alpine meadows and mountain huts serving dumplings and strudel. In summer it’s a hiker’s paradise of cable cars and high trails; in winter it’s world-class skiing. It’s the antidote to hot-city sightseeing — cool, dramatic, and unlike anywhere else in the country.

Basilicata — the road less travelled

If you want the Italy of a generation ago, go to Basilicata. Its star is Matera, a city of ancient cave dwellings (the Sassi) carved into a ravine — once a symbol of southern poverty, now one of the most extraordinary places to stay in Europe. Beyond it lies a wild, empty, mountainous region that sees a fraction of the visitors it deserves. This is deep-south Italy, unpolished and unforgettable.

Emilia-Romagna — the country’s kitchen

If your second trip is really about the food — and for many people it is — this is the region. Emilia-Romagna gave the world Parmigiano-Reggiano, prosciutto di Parma, real balsamic vinegar, and the slow ragù that the rest of the planet flattened into “spag bol.” Base yourself in handsome, arcaded Bologna and eat your way outward through Parma and Modena. It’s prosperous, welcoming, and gloriously under-touristed given what’s on the plate.

How to choose between them

Don’t agonise — match the region to the trip you want:

Food and wine above all: Emilia-Romagna or Piedmont.
Sun, sea and easy days: Puglia.
History and big flavours: Sicily.
Mountains and cool air: the Dolomites.
Off the map entirely: Basilicata.

Getting there is easier than you’d think

The instinct is to assume these places are hard to reach. Mostly they’re not. Regional airports (Bari for Puglia, Palermo and Catania for Sicily, Bologna for Emilia-Romagna, Turin for Piedmont) put you close, and Italy’s trains reach far more of the country than first-timers realise. The pattern that works: fly or train into the region, then rent a car for the rural stretches and drop it before any city — the same rule that serves you everywhere in Italy.

The point of a second trip

The first trip proves you love Italy. The second proves how much of it there is to love. Pick one of these, settle in for a week, and you’ll come home having seen an Italy most visitors never do — and already plotting the third. That’s the quiet trap of this country: there’s always one more region worth a week of your life.