Matera, Basilicata: a city carved into stone
Matera's Sassi are cave dwellings continuously inhabited for 9,000 years, making it one of the oldest cities on earth. UNESCO restored the abandoned caves into hotels and restaurants. Stay at Sextantio Le Grotte della Civita to sleep in a candlelit cave room. Walk the Sasso Caveoso at sunset when the limestone glows amber. Matera was a film location for the most recent James Bond opening sequence and for Mel Gibson's Passion. Reach it by car or train via Bari, three hours from Rome.
Lecce, Puglia: the Florence of the South
Lecce is a Baroque masterpiece in soft golden limestone, with churches and palaces so ornate they look unreal in evening light. The historic centre is small and walkable, with extraordinary food (orecchiette pasta, puccia bread, pasticciotto pastries) at a fraction of Tuscan prices. Use Lecce as a base for the Salento peninsula: Otranto on the Adriatic, Gallipoli on the Ionian, the white town of Ostuni an hour north. Late spring and early autumn are ideal. Avoid August unless you book six months out.
Orvieto, Umbria: a city on a cliff
Orvieto sits on a flat plug of volcanic tuff, accessed by a funicular that climbs from the train station to the medieval centre. The Duomo is one of the great cathedral facades in Italy, often empty in the morning. Beneath the city is a network of Etruscan tunnels and wells you can tour. Day-trip from Rome by train (75 minutes) or use Orvieto as a base to explore Civita di Bagnoregio (the dying city, accessed by a footbridge) and the Umbrian wine country.
Bologna, Emilia-Romagna: the food capital
Italians widely regard Bologna as the country's best food city. Tagliatelle al ragu, mortadella, tortellini in brodo, and the bolognese tradition all originate here. The historic centre has the longest covered arcades in Europe (37 kilometres) and a leaning tower most tourists overlook. Day trips reach Modena (balsamic vinegar, Ferrari museum), Parma (prosciutto and parmigiano), and Ravenna (the most extraordinary Byzantine mosaics in the world). Bologna is a 35-minute train ride from Florence and a totally different city.
Trieste, Friuli-Venezia Giulia: Italy meets Vienna
Trieste was the main port of the Austro-Hungarian Empire and looks more Viennese than Italian. Coffee culture is religious here: the historic cafes (Caffe San Marco, Caffe degli Specchi) once hosted James Joyce, Italo Svevo and Sigmund Freud. The seafront Piazza Unita d'Italia is the largest sea-facing square in Europe. Trieste sits 5 kilometres from Slovenia, making it the natural launching point for trips into the Karst plateau and Slovenian wine country.
Procida, Bay of Naples: the colourful island
Procida is a 40-minute ferry from Naples and a different world from neighbouring Capri and Ischia. The fishing village of Marina Corricella is a tumble of pastel-painted houses around a tiny harbour, with lemon-grove restaurants serving spaghetti alle vongole at almost local prices. The whole island is walkable in a day. Stay overnight to experience the empty evening streets after the day-trippers leave. Procida was Italian Capital of Culture in 2022 but remains uncrowded compared to its famous neighbours.
Asolo, Veneto: the city of a hundred horizons
Asolo is a hill town an hour north of Venice that the writer Robert Browning called the most beautiful place he had ever seen. The medieval centre is preserved in cobblestone, with two squares, a Roman aqueduct, and views over the Veneto plain that genuinely take the breath away. Use Asolo as a base for the Prosecco hills (a UNESCO landscape an hour west) and the Palladian villas of the Brenta canal. The town empties in winter, which is when locals say it is at its best.
Bergamo, Lombardy: a walled city above Milan
Bergamo Alta is a perfectly preserved Venetian-walled hill town 50 minutes from Milan by train and bus. The old city sits high above the modern lower town, accessed by a funicular that climbs into the medieval streets. Piazza Vecchia is one of the most harmonious squares in Italy. Eat the local casoncelli pasta and polenta with a Valcalepio red. Bergamo's small airport is a hub for European budget airlines, making it a smart entry point for a Northern Italy trip.
Sulmona, Abruzzo: pasta, mountains and silence
Sulmona is the geographic centre of the wild Abruzzo national park region, a town of pink-stone medieval streets famous for confetti (sugared almonds) and its Roman aqueduct. From Sulmona you reach the Maiella mountains, the abandoned village of Pacentro, and the wild brown bears that still live in the Abruzzo backcountry. Two hours from Rome by train, the area is spectacularly underused by international travellers.
Cefalu, Sicily: a beach town that earns its postcards
On Sicily's northern coast, an hour east of Palermo, Cefalu has a Norman cathedral on Europe's most cinematic main square, a long sandy beach, and a medieval old town that compresses an entire seaside Sicily fantasy into a few cobbled streets. The town is busy in July and August but blissfully calm in May, June, September and October. From Cefalu, day trips reach the Madonie mountains, Tindari, and the Aeolian island ferries from Milazzo.
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