Umbria sits in the green heart of Italy, largely overlooked by travellers who rush between Rome and Florence without realising what lies between them. We spent six nights moving through it slowly — from the Tuscan border down through Perugia and on to Gubbio — and came away with the particular satisfaction of a trip that exceeded every expectation we had brought with us.
Agriturismo La Terra — On the Tuscan Border
We began at Agriturismo La Terra, a working farm sitting on the border between Tuscany and Umbria, where we stayed for two nights. The setting alone would have been enough — rolling hills, olive groves, the kind of view that makes you want to sit outside with a glass of wine and do absolutely nothing. But La Terra offered something more than scenery.
The owner ran a four-course cooking class that was one of the highlights of the entire trip. We cooked in his kitchen, learning the rhythms of a regional Italian meal — the pasta made by hand, the sauces built slowly, the way each course is given its proper time and attention. We ate what we had made, at a long table, with wine poured generously. And then, when the meal was done and the evening had settled into something unhurried and warm, he brought out his own homemade limoncello and grappa — digestivi he had made himself — and we sat a while longer. It was the kind of hospitality that cannot be manufactured.
Each morning we drove out to explore the surrounding towns — the kind of quiet, unhurried hilltowns that Umbria does better than almost anywhere in Italy. No queues, no tour buses, just stone streets and good coffee and the sense that ordinary life was carrying on around you.
Perugia
From La Terra we moved to Perugia for two nights, staying in town at La Rosetta, a classic hotel in the heart of the old city. Perugia is the regional capital of Umbria and it carries that status with a certain confidence — it is a proper city, with a university, a serious food culture, and a medieval centre that rewards exploration on foot.
The hotel itself was a pleasure to return to each evening. The bar was run by bartenders who took their craft seriously, and the atmosphere was warm and lively without being loud — the kind of bar where you order one drink and find yourself staying for two. Whenever you ordered, something to eat arrived alongside without being asked for — the kind of hospitality that is welcomed but never expected. The beds were among the most comfortable we slept in on the entire trip, and despite being in the centre of the city the hotel was quiet and peaceful once the evening settled.
We spent our days simply walking. The Corso Vannucci, the main pedestrian street, runs along the spine of the hilltop and opens onto the Piazza IV Novembre, where the great Gothic fountain and the Palazzo dei Priori face each other across the square. In the evenings the square fills with students and locals and the atmosphere is entirely different from the daytime — more relaxed, more alive. We found many good restaurants over the two days — one down a flight of steps into a cellar, a small local hangout where the truffle pasta was exceptional, and a street vendor selling porchetta and other panini sandwiches that were as good as anything we ate sitting down.
Gubbio and the Winery
Our final two nights were in Gubbio, one of the best-preserved medieval towns in Italy, where we stayed at the Park Hotel ai Cappuccini — a converted Franciscan monastery set just outside the town walls, with beautiful grounds and the kind of quiet that a former monastery earns naturally.
Gubbio itself is extraordinary. The town climbs steeply up the hillside, its stone buildings stacked one above the other, and the Piazza della Signoria — suspended on a terrace halfway up the hill — is one of the most dramatic public spaces in Umbria. It is the kind of town that makes you feel the weight of centuries in a way that is quietly humbling rather than overwhelming.
The finest afternoon of the trip was a visit to Azienda Agraria Semonte, a local winery just outside Gubbio. We were the only people there, which gave the whole experience a quality that no organized tour could replicate — it felt entirely private, entirely catered to us. We tasted through their wines at our own pace, paired with charcuterie and freshly baked focaccia that had clearly been made that morning. The conversation was unhurried, the setting was beautiful, and by the end of it we had bought wine and olive oil to bring home. It is exactly the kind of afternoon that travel in this part of Italy is made for.
We were the only people at the winery. The focaccia was still warm. The wine was extraordinary. Some afternoons in Italy simply cannot be improved upon.
Agriturismo La Terra is worth booking well in advance — the cooking class fills quickly and it is not the kind of experience you want to miss. Perugia works well as a two-night base for the central part of the region. Gubbio is quieter and less visited than it deserves to be; the Park Hotel ai Cappuccini is a genuinely special place to stay. Allow at least six nights to move through the region without rushing.