The Best Cities Off the Beaten Path to Visit in Italy

Italy's most celebrated cities need no introduction. But for the traveller who seeks depth over popularity — who values the silence of a piazza at dawn over the choreography of a queue — there exists another Italy entirely. These are five of its finest chapters.

Basilicata

Matera

"A city that was never built — it was excavated, carved from the living rock over three thousand years of uninterrupted human presence."

Matera is not a destination so much as a revelation. Cascading down the walls of a limestone ravine in the deep south of Italy, its Sassi — ancient cave dwellings that constitute one of the world's oldest continuously inhabited settlements — earned the city its UNESCO designation long before European Capital of Culture status brought it, briefly, to wider attention.

What makes Matera exceptional for the discerning traveller is precisely what the crowds cannot disturb: the primordial silence that settles after dark, the extraordinary geology of the Murgia plateau across the ravine, the intimacy of dining inside a 9th-century rupestrian church converted into a private dining room. The city operates on geological time, and it rewards those who slow down to match its rhythm.

Stay at one of the exquisitely restored sassi suites — where bare tufa walls, vaulted ceilings, and natural cisterns become the architecture — and you will understand why Norman Lewis once called southern Italy the last truly wild corner of Europe.

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Arrange a private torchlit walk through the Sasso Caveoso after midnight, when the city empties and the ancient city glows like embers. Few experiences in Italy feel as close to time travel.

Friuli-Venezia Giulia

Trieste

"A Habsburg port city on the Adriatic edge, where Italian sensibility, Central European architecture, and a restless literary spirit converge in a way that exists nowhere else."

James Joyce wrote much of Ulysses here. Rainer Maria Rilke found his castle on the cliffs above the bay. Jan Morris called it her favourite city in the world. Trieste has always attracted those who see past surfaces — and it continues to reward them.

The city operates outside Italy's standard tourist geography, sitting at the very tip of a peninsula between Slovenia and the Adriatic. Its architecture is grandly Viennese, its coffee culture the most serious in the country (Trieste consumes more coffee per capita than any other Italian city), and its literary cafés — most notably the legendary Caffè San Marco — remain alive as gathering places for conversation rather than monuments to nostalgia.

The Carso plateau above the city offers dramatic walking through limestone karst, while the Castello di Miramare — a 19th-century palace perched above the sea — provides one of the most cinematic settings in northern Italy. For collectors and connoisseurs, Trieste's antique dealers and its small but exceptional contemporary art scene represent some of Italy's most overlooked opportunities.

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Commission a private tasting of Carso wines — volcanic, mineral, and fiercely local — paired with Adriatic seafood at a table overlooking the Gulf of Trieste as the sun sets behind Slovenia. This is Italy's most overlooked wine country.

Puglia

Lecce

"Called the Florence of the South — though it is, in truth, entirely its own: a baroque city of such extravagance and warmth that it seems to defy the laws of stone."

Lecce's soft local limestone — pietra leccese — is so workable that 17th-century architects essentially used it as an outdoor canvas. The result is a city where every church façade, palazzo cornice, and doorway erupts with garlands, cherubs, sea monsters, and foliage in a baroque exuberance unmatched anywhere in Europe. This is not ornament as decoration; it is ornament as philosophy.

Beyond the architecture, Lecce is one of Italy's great food cities — a fact its residents have always known and the rest of the country is slowly acknowledging. The pasticciotto, the local pastry filled with custard cream, consumed standing at a marble bar with a proper espresso, is one of the small perfect rituals that define Italian travel at its best. The local olive oil, produced from centuries-old trees twisted into extraordinary forms across the Salento plain, is among the finest in the Mediterranean.

Lecce rewards slow exploration on foot, late dinners at tables set in cobbled courtyards, and mornings spent with a local guide who can unlock the private gardens and the noble palazzi that never appear in guidebooks.

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Arrange access to a private palazzo in the centro storico for your stay — many of Lecce's finest aristocratic residences are available exclusively through curated contacts. Sleeping within those frescoed walls is an entirely different experience from any hotel.

Le Marche

Ascoli Piceno

"A city built almost entirely of travertine marble, set in the crease of two rivers between the Apennines and the Adriatic — and almost entirely unknown to the world beyond Le Marche."

Ascoli Piceno possesses one of Italy's most beautiful main squares — the Piazza del Popolo — a fact that its inhabitants know perfectly well and international visitors have barely begun to discover. Enclosed by Renaissance arcades and presided over by the Church of San Francesco and the 13th-century Palazzo dei Capitani, the piazza glows at dusk with a warm, honeyed light reflected off its travertine surfaces that has no equivalent in Italy.

The city is compact, walkable, and deeply authentic. It has not reorganised itself around tourism, which means its bars, restaurants, and shops serve the people who live here. The olive ascolane — large local olives stuffed with a seasoned meat filling, breaded and fried — were invented here and are eaten here with a quality that no imitation has ever equalled.

The surrounding landscape — rolling hills, medieval hill towns, the Sibillini mountains within easy reach — makes Ascoli Piceno an ideal base for exploring one of Italy's least-visited and most rewarding regions. It is, in the truest sense, what the guidebooks used to call "unspoiled."

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A private helicopter transfer from Rome or Florence, combined with a curated itinerary through the hill towns of Le Marche, transforms what would be a difficult drive into one of Italy's great aerial experiences — the Apennine landscape seen from above is extraordinary.

Sicily

Noto

"Perhaps the most perfect baroque city in the world — rebuilt from nothing after the 1693 earthquake by architects who treated catastrophe as a commission."

When the earthquake of 1693 destroyed the original Noto entirely, the decision was made not to rebuild on the ruins but to start again — three kilometres away, on a new site, with a blank plan and a Baroque ambition that bordered on the visionary. The result, completed over forty years, is a city of breathtaking coherence: a single golden limestone theatre, its main street a sequence of aristocratic palazzi and church façades that seem lit from within, its urban geometry so assured that it functions as a single work of architecture.

Noto is small enough to walk end to end in twenty minutes and large enough to absorb days of attention. Its almond granita — white, intensely flavoured, consumed with a warm brioche col tuppo at a marble bar — is one of the defining tastes of Sicilian civilisation. Its surrounding Val di Noto countryside, planted with citrus groves, olives, and vineyards producing some of Sicily's finest Nero d'Avola, is among the most beautiful agricultural landscapes in the Mediterranean.

For the luxury traveller, Noto and the surrounding Baroque triangle — Ragusa Ibla, Modica, Scicli — represent Sicily at its most refined and its most itself: ancient, golden, and entirely without compromise.

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Secure exclusive access to a restored masseria or baroque villa in the Val di Noto countryside — several exceptional properties offer private buyout for small groups, combining vineyards, infinity pools, and proximity to Noto, Ragusa, and Modica in one of Italy's most cinematic settings.

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