The standard Italian fortnight is Rome, Florence and Venice, and there is nothing wrong with it except that all three are at or beyond capacity for most of the year, and the version of Italy you get is the one that has been packaged for exactly that trip.
The south is a different country. It is poorer, hotter, slower, and the food — which is what most people actually come for — is better and about half the price.
Fourteen nights, by train and bus with one hire car.
Days 1–3: Naples
The most alive city in Italy and the one people are most nervous about. It is fine; it is chaotic, loud and worn, and it has more going on per street than anywhere else in the country.
The Museo Archeologico Nazionale holds everything portable that was excavated from Pompeii and Herculaneum, and going here before the sites transforms them.
Spaccanapoli and the Quartieri Spagnoli. Cappella Sansevero for the Veiled Christ, which is a genuinely astonishing piece of marble carving — book ahead.
Pizza. Naples invented it and the difference is real. Da Michele, Sorbillo, Di Matteo — expect a queue and a wait and a bill under ten euros.
Herculaneum rather than Pompeii, or as well: smaller, better preserved, with wooden beams and upper floors intact, and a fraction of the visitors.
Days 4–5: the coast, but not Amalfi
The Amalfi Coast in summer is a single-lane road with a traffic jam on it. Two alternatives:
The Cilento, south of Salerno — a national park with the Greek temples at Paestum, which are better preserved than almost anything in Greece, empty beaches and buffalo mozzarella made where it is from.
Procida, the smallest island in the Bay of Naples, which was Italy’s capital of culture in 2022 and still receives a tiny fraction of Capri’s traffic.
If you must do Amalfi: go in April or October, stay in Atrani rather than Positano, and use the ferries rather than the road.
Days 6–7: Matera
Inland, in Basilicata, and one of the strangest places in Europe.
The Sassi are cave dwellings carved into a ravine, continuously inhabited for around nine thousand years, which makes Matera among the oldest inhabited settlements on earth. In the 1950s the caves were declared a national disgrace and the population was forcibly rehoused. They were re-occupied from the 1980s and the town was European Capital of Culture in 2019.
Stay in a cave hotel. Walk the ravine on the far side at dawn, when the whole town is lit sideways.
Days 8–10: Puglia
The heel. Hire a car here; the region is spread out and the trains are slow.
Alberobello for the trulli, conical drystone houses, which is touristed and worth an hour. Locorotondo and Ostuni, whitewashed hill towns, are better.
Lecce — extravagant baroque in soft golden limestone, and a university town, so it has life outside the season.
The Salento coast — Otranto, Santa Maria di Leuca, and beaches on both the Adriatic and Ionian sides within twenty minutes of each other.
Eat: orecchiette con cime di rapa, burrata where it is made, and pasticciotto for breakfast.
Days 11–14: Sicily
Fly or take the overnight train and ferry from the mainland — the train is loaded onto a boat, which is a genuinely odd experience.
Four days does one corner. Choose:
The east: Catania, built from black lava; Etna, which you can be driven a long way up; Taormina, beautiful and overrun; Syracuse and Ortigia, which is the best base in Sicily — a Greek colony that rivalled Athens, on an island connected by three bridges, with a cathedral built inside a Doric temple.
The west: Palermo, which is Naples’ equal for chaos and has the best street food in Italy; Monreale’s Norman-Arab-Byzantine mosaics; Segesta and Selinunte’s Greek temples; Trapani and the salt pans.
Practical
Trains are good between the major southern cities and slow in Puglia and Sicily. Book high-speed services in advance for the cheap fares; regional trains are fixed-price and need no booking.
A car for two or three days in Puglia and in Sicily. Avoid driving in Naples and Palermo entirely.
ZTL zones — restricted traffic areas in the centre of almost every Italian town — are camera-enforced and the fines arrive months later via the rental company. If your hotel is inside one, they must register your plate.
Season: April–June and September–October. July and August in the south are 38°C and up, and August is when Italy itself goes on holiday.
Sunday and Monday closures are widespread for museums and family restaurants. Check before building a day around one.
If you would rather have the north
The same principle applies further up: Bologna and Emilia-Romagna for the best food in Italy and a fraction of Florence’s crowd; the Marche, which is Tuscany twenty years ago; Friuli and Trieste, which are Italian, Slovene and Austrian at once; and the Dolomites, which are the best mountain walking in the country and are largely German-speaking.
Any of those can replace the Sicily leg without changing the logic of the trip.