Umbria: Truffles, Medieval Towns and the Wine Beyond Tuscany

People say “Tuscany” and mean a particular Italy: the cypress trees, the wine road, the hill towns they have read about since university. Umbria is the answer to that. Immediately south of Tuscany, sharing its hills and its light and its pace, it has the equivalent landscape and the superior food culture and approximately one tenth of the visitors. It is the only landlocked region on the Italian peninsula: no coastline, no foreign border, surrounded on all sides by other Italian regions. It was never on the route to anywhere else. You come here on purpose or you do not come at all. Most people do not come at all.

That is changing, and the question is whether to arrive before or after the change completes. My position is before. The norcinerie of Norcia, the truffle hunters of the Valnerina, the Sagrantino producers of Montefalco: these are people who have been working their particular craft for generations without international attention, and the quality reflects the conditions. When the attention comes, the character changes. It is not a theory. It is what happened to Tuscany.

Italy Charme offers four ways in: the Chocolate Cooking Class in Perugia (€290/pp), the Beyond Tuscany tour (€5,500/pp), the Luxury in the Italian Heartland tour (€6,500/pp), and the Villa in Winery (€1,200/pp) at a working Umbrian estate. The tour name “Beyond Tuscany” is what I think every time a client tells me they have already done Siena and Montepulciano and want something quieter. Umbria is the answer to that conversation.

Assisi. The birthplace of St. Francis (1182) and St. Clare. UNESCO World Heritage since 2000. The Basilica di San Francesco is built in two levels: the Upper Basilica contains Giotto’s celebrated cycle of the Life of St. Francis, painted in the 1290s, the work that shifted European painting from Byzantine formality toward naturalism. The Lower Basilica is older, darker, and more devotional, with frescoes by Cimabue, Pietro Lorenzetti, and Simone Martini. Most visitors spend ninety minutes here. I recommend four hours, minimum, and a return the following morning when the light in the Upper Basilica is different.

Orvieto. Built on a volcanic tufa cliff above the Paglia valley, with more than 1,200 caves and tunnels cut into the rock beneath the city over three millennia. The Duomo was begun in 1290 and contains, in the Cappella di San Brizio, Luca Signorelli’s frescoes of the Last Judgment (1499–1504). Art historians have confirmed for five centuries that these works directly inspired Michelangelo’s Sistine Chapel. Then there is the Pozzo di San Patrizio: a well commissioned in 1527 by Pope Clement VII from architect Antonio da Sangallo the Younger, completed 1537. The engineering is a double helix: two completely separate spiral staircases of 248 steps each, one for descent and one for ascent, so the donkeys carrying water to the surface never encountered the empty donkeys going down. This solved a hydraulic problem in the same decade that Michelangelo was painting in Rome. Both things were happening simultaneously in central Italy.

Spoleto. The Ponte delle Torri is an aqueduct-bridge from the 14th century, 230 metres long and 80 metres high, spanning a valley outside the walls. It is the kind of structure that makes you stop the car and stand in silence for a moment. Inside the Duomo, the apse fresco of the Life of the Virgin was commissioned from Filippo Lippi around 1467. Lippi died in Spoleto on October 8, 1469 before the work was complete. It was finished by his workshop, including Fra Diamante and the young Filippino Lippi (Filippo’s son, approximately twelve years old when his father died). Every June and July, Spoleto hosts the Festival dei Due Mondi (Festival of Two Worlds), founded in 1958 by composer Gian Carlo Menotti, one of Italy’s most prestigious performing arts events.

Gubbio. One of the best-preserved medieval towns in Italy, and the location of the Eugubine Tablets: seven bronze tablets from the 3rd to 1st century BC containing the longest surviving text in the Umbrian language, one of the most important pre-Roman inscriptions on the peninsula. They are held at the Palazzo dei Consoli, which overlooks Piazza Grande, considered among the finest medieval piazze in Italy. Every May 15, Gubbio holds the Corsa dei Ceri (Race of the Candles), a festival with 900 years of continuous history honoring Sant’Ubaldo. In October and November, the hills around Gubbio produce white truffles (Tuber magnatum pico), the season running through December.

Spello. Roman walls from the Augustan era still surround most of the town. In the Church of Santa Maria Maggiore, the Baglioni Chapel contains Pinturicchio’s frescoes, completed in 1501, among the finest Renaissance frescoes in Umbria and the reason Spello is worth a full morning. In late May or June, for Corpus Christi, the streets of Spello are carpeted with elaborate designs made from flower petals (the Infiorata): a week-long event centered on the Sunday of Corpus Christi that has been happening here since the 18th century.

Perugia. The regional capital, and the Galleria Nazionale dell’Umbria holds the most important collection of Umbrian painting in existence, including major works by Perugino (who taught Raphael) and Pinturicchio. The Fontana Maggiore in Piazza IV Novembre was sculpted between 1275 and 1278 by Nicola and Giovanni Pisano, father and son, and is one of the finest medieval sculptures in Italy. Perugina, the chocolate company, was founded here in 1907. Luisa Spagnoli created the Baci chocolate in the early 1920s. Every October, Perugia holds Eurochocolate, one of Europe’s largest chocolate festivals. Our Chocolate Cooking Class (€290/pp) is built directly from this tradition.

Todi. A compact, self-contained medieval hilltop town overlooking the Tiber valley. In the 1990s, Richard S. Levine, a professor of Architecture at the University of Kentucky, used Todi as a case study model for sustainable urban design in his academic work. The Italian press then widely reported Todi as “the world’s most livable city.” The characterization stuck and circulated globally. It was not quite accurate: Levine used Todi because it had the qualities he was studying, not because a competitive index had ranked it first. That is a more interesting story than the headline. Todi is worth visiting because it is in practice self-contained and beautiful, not because a Kentucky professor said so in an academic paper.

Montefalco. Called “La Ringhiera dell’Umbria” (The Balcony of Umbria) for its hilltop panorama across the Spoleto valley and the surrounding hills. It is the gateway to Sagrantino wine country, and the town itself holds a Museo Civico with Benozzo Gozzoli frescoes in the former church of San Francesco. Our Villa in Winery is rooted in the Montefalco zone.

A norcino is a butcher specializing in pork. The word exists in the Italian language nationally, used in every region, and it derives entirely from the town of Norcia. Historically, the skilled pork butchers of Norcia traveled throughout the peninsula each autumn to slaughter and cure, and the quality of their work was so consistently superior that their hometown name became the generic term. A butcher in Turin who works with pork may be called a norcino with no irony and no connection to Umbria. This tells you everything you need to know about the reputation.

The norcinerie of Norcia produce sausages, cured hams, mazzafegato (pork liver sausage), lard, and various salumi to IGP standards. The Castelluccio lentils are a separate story: small lentils with the IGP designation (since 1997), grown only on the Piano Grande plateau at 1,452 metres altitude within the Monti Sibillini National Park. The altitude and temperature extremes produce a skin so thin that the lentils require no pre-soaking before cooking. They are grown at the edge of what cultivation is possible in Italy, and the result is a product unlike anything at lower elevations.

Every year, from late May into early July, the Piano Grande flowers. The lentil, wheat, and wildflower crops bloom simultaneously across the plateau in a mosaic of red, yellow, blue, and white: the Fioritura, a natural phenomenon that draws photographers from across Italy and that no competitor, to my knowledge, has ever mentioned in a luxury travel context. The exact peak varies by a week or two each year; late June is typically the most intense.

On wine: Sagrantino di Montefalco DOCG is one of Italy’s most demanding and age-worthy reds. The Sagrantino grape grows in serious commercial quantities almost exclusively in the zone around Montefalco. It is essentially a geographically specific variety in a way that Sangiovese and Nebbiolo are not. DOCG status since 1992. Minimum aging: 37 months total, including 12 months in oak barrels and 4 months in bottle. The wine that emerges is structured, tannic, and extraordinary with time. The modern reputation was built largely by Marco Caprai, who took over his family’s estate in 1988 and, over the following decade, demonstrated what Sagrantino could become. His “25 Anni” bottling, debuting with the 1993 vintage, established international recognition.

Alongside Sagrantino: Rosso di Montefalco DOC (the more accessible, younger expression from the same zone), Grechetto (Umbria’s signature white grape, almondy and mineral), and Orvieto Classico DOC (primarily Grechetto and Trebbiano Toscano, a white wine made here since Etruscan times). The Lungarotti estate near Perugia operates the Museo del Vino di Torgiano (MUVIT), one of Italy’s first and most important wine museums, founded by the Lungarotti Foundation in 1974. Our Beyond Tuscany tour (€5,500/pp) moves through this food and wine culture with depth. The Villa in Winery (€1,200/pp) puts you inside it.

Three truffles, three seasons. Black truffle (Tuber melanosporum) from the Norcia and Spoleto area and the Valnerina valley to the south: peak season November through March, with major fairs in Norcia in February and March that draw buyers from across Europe. White truffle (Tuber magnatum pico) from the hills around Gubbio: season October through December, less famous than Alba in Piedmont but genuine. Summer black truffle (Tuber aestivum or uncinatum): July through September, less intense in flavour than the winter variety but accessible and appropriate for cooking rather than shaving raw.

The tartufaio (the licensed truffle hunter) works with a trained dog. Pigs have not been used in professional truffle hunting for decades; the dog is faster, more precise, and does not eat the truffle on finding it. The relationship between a tartufaio and a trained dog is close, developed over years, and the dog’s nose is the entire business. A private truffle hunt with a licensed tartufaio in the Norcia area or the Gubbio hills is the experience I recommend most often to first-time Umbria visitors who want to understand the food culture at its source. It lasts two to three hours, usually ends at the hunter’s kitchen, and produces a meal that has no equivalent in a restaurant.

Norcia has two identities. The first is the norcineria I described above: the cured pork capital of Italy, the town whose name became a word. The second is St. Benedict of Norcia, born here around 480 AD, whose Rule governing monastic life became the foundation of Western monasticism. The Benedictine order spread across Europe and preserved classical learning through the Dark Ages. Norcia produced the man who made that possible. The Basilica di San Benedetto marks his birthplace in the centre of town.

On August 24, 2016, a magnitude 6.0 earthquake struck central Italy. On October 30, 2016, a magnitude 6.6 earthquake struck the same area. The Basilica di San Benedetto was almost completely destroyed on October 30. The façade survived intact. Everything behind it collapsed. The historic centre of Norcia was severely damaged. The norcinerie opened the following day. They did not close.

What I have not seen in any competitor’s content, and what I consider the most important travel story in Umbria right now: on October 31, 2025, the Basilica of San Benedetto in Norcia reopened for worship. Nine years after its destruction. A €15 million reconstruction used original materials where possible combined with earthquake-resistant engineering. Archbishop Renato Boccardo dedicated the rebuilt church. The town is not yet what it was before 2016, but the basilica is back, and the norcinerie are still there, and the truffles are still in the Valnerina. Norcia before the earthquake was moving. Norcia now, with the basilica returned, is something different. There is a resilience there that you feel when you walk in. I send clients now, not later.

The Luxury in the Italian Heartland tour (€6,500/pp) includes Norcia as a central element, not as an aside.

Spring (April through June) and autumn (October through November) are both strong. Spring brings the Corsa dei Ceri in Gubbio on May 15, the Infiorata di Spello for Corpus Christi in late May or June, the Fioritura at Castelluccio beginning in late May and peaking in late June, and the Festival dei Due Mondi in Spoleto from late June into July. The green hills are at their most saturated in April and May. The towns are accessible without the competition of August.

Autumn brings the white truffle season around Gubbio from October, the Eurochocolate festival in Perugia in October, the Sagrantino harvest at Montefalco, and the black truffle season beginning in November. The foliage across the green hills in October and November is the equivalent of what New England offers, without the crowds. This is when I go myself, when I can.

Winter, specifically February and March, has an argument that almost nobody makes: the black truffle is at its peak, the Norcia fairs are the most important of the year, the hilltop towns have no visitors at all, and the norcinerie are fully stocked. Cold, yes. Atmospheric, unquestionably. If truffle hunting and cured pork are the primary objectives, February in Umbria outperforms any other month in any other region.