Italy has always rewarded those who approach it with genuine attention. The country is not a single experience but a sequence of distinct worlds, each with its own register, its own food, its own particular relationship with beauty. To travel it well is to resist the urge to see everything and instead to understand something. Here is a journey through some of those worlds — from the shores of Lake Como to the castles of Emilia-Romagna, to Florence and the Tuscan countryside, and finally to the green hills of Umbria.
We begin at Lake Como, which has earned its reputation honestly. The combination of alpine drama and Mediterranean warmth, the light on the water in the early morning, the gardens that spill down toward the lake from villas that have been here for centuries — these things are as good as advertised. The Grand Hotel Tremezzo, with its century of lakeside hospitality, remains a benchmark. Its sister property Passalacqua, created by Valentina De Santis inside an immaculately restored 18th-century villa once visited by Napoleon and Churchill, offers a different texture — more intimate, more personal, with interiors that carry the wit and colour of La DoubleJ. Other fine choices on the lake include Villa d’Este and the Mandarin Oriental Lago di Como, each with its own distinct character.
From Como we travel east and south to Emilia-Romagna, and to a discovery that changes how most travelers understand Italy. This is the region that produces Parmigiano-Reggiano, Prosciutto di Parma, Aceto Balsamico Tradizionale, Lambrusco, Ferrari, Lamborghini, and Maserati — an improbable combination that makes perfect sense once you have spent time here and understood the regional character: an obsessive, quietly proud commitment to doing things exceptionally well.
In the foothills of the Apennines, between Parma and Reggio Emilia, Relais Roncolo 1888 is the estate that most fully embodies what makes this region unlike anywhere else. Arriving along the estate’s cypress-lined road, through 130 hectares of certified organic land farmed continuously since 1888, the experience is of arrival in a place with its own deep internal life — not a hotel dressed as an estate, but an estate that decided, at some point, to welcome guests. The 17 rooms distributed across the historic hamlet are each distinct. Ristorante Limonaia draws from the estate’s own production and from the extraordinary culinary heritage of Emilia-Romagna. The wines are those of Venturini Baldini, one of the finest organic producers in the region. The experience of staying here is of Emilia-Romagna understood from within — its food, its landscapes, its particular tempo.
Beyond Roncolo, Emilia-Romagna rewards exploration. In Modena, Casa Maria Luigia — the boutique hotel of Massimo Bottura and Lara Gilmore — offers the ideal complement to a meal at Osteria Francescana. The Motor Valley provides one of Italy’s most thrilling non-culinary experiences: factory visits and driving experiences at Ferrari (Maranello), Lamborghini (Sant’Agata Bolognese), and Maserati (Modena). The medieval castles of the Reggiano hills, the balsamic producers of Canossa, the food markets of Parma — each layer of the region reveals another.
No Italian itinerary can omit Florence, and none should try. The city carries the full weight of the Renaissance in a compact historic centre that rewards walking at almost any hour. Michelangelo’s David. Botticelli’s Venus and Primavera in the Uffizi. Brunelleschi’s dome, which remains one of the great engineering achievements in the history of architecture. The Palazzo Strozzi, which consistently presents some of Europe’s most ambitious temporary art exhibitions. And the Gucci Garden in the Piazza della Signoria, a permanent museum-boutique that traces the house’s creative history with genuine curatorial intelligence.
For accommodation, the Four Seasons Hotel Firenze — set across a 15th-century palazzo and a private garden — remains the gold standard for scale and service. Portrait Firenze, the Lungarno Collection property on the Arno, offers a more intimate alternative with exceptional views. The city rewards an extra night: the morning light in the Oltrarno, the restaurants that open only in the evening, the discovery that Florence at 7am, before the tours begin, is a different city entirely.
South of Florence, through Siena and into the Val d’Orcia, Tuscany reveals its deepest character. The landscape here — UNESCO-listed, composed with an almost supernatural sense of proportion — is the Italy of collective imagination: cypress-lined roads, hilltop towns, vineyards in the exact shades of green and gold that painters have been trying to capture for six hundred years. Rosewood Castiglion del Bosco, the Ferragamo family’s estate in the Val d’Orcia, offers one of the most complete experiences in Tuscan luxury: a private wine estate, a Michelin-starred restaurant, and access to a landscape that feels genuinely untouched. Smaller properties such as Borgo Pignano — a 750-acre organic estate near Volterra, documented since 1139 — offer a more intimate encounter with the region.
On the Tuscan coast, Porto Ercole and the Argentario have long served as the summer retreat of a certain Italian elegance. Il Pellicano, perched above the sea, has maintained the particular glamour of the post-war Mediterranean — a place where Charlie Chaplin, Sophia Loren, and Slim Aarons’ subjects once gathered, and where the spirit of that era persists in the architecture and the light.
Our journey concludes in Umbria — landlocked, green, and utterly its own. Where Tuscany has become the default Italian countryside experience, Umbria remains the authentic version: fewer tourists, deeper quiet, hill towns that function as communities rather than attractions. The Castello di Reschio — a medieval castle restored over decades by the Bolza family into a luxury estate of exceptional integrity — is the finest introduction to what Umbrian hospitality can be at its best.
Italy, traveled well, is not a checklist. It is a series of recalibrations — of expectations, of pace, of what “beautiful” means when you are standing in the right place at the right hour. Each of the stops on this journey offers that experience. Together, they offer something closer to an understanding of why Italy, for so many travellers, remains the answer to a question that keeps being asked anew.
More time at the table. More walks through the vines. More of everything Roncolo does best. Stay four nights in April or May — pay for three
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