The best hidden hill towns with a medieval festival within 90 minutes of Perugia

Cetona

Why visit Cetona

The town sits on the western flank of a ridge at the meeting point of Toscana, Umbria and Lazio, where the mountain divides the Val d'Orcia from the Val di Chiana. The medieval comune passed between Siena, Orvieto and Perugia before falling to Siena in the late fourteenth century, and it was Cosimo I who later sold it whole to a marchese.

The fortress at the top of the grid and the square laid out below it are two halves of the same Renaissance move: a private residence replacing a garrison at the summit, a flat civic stage opened up at the base. Above the town, in the woods, the hermitage and the caves belong to a much older layer, human use of the mountain reaching back to the Mesolithic, long before any comune or marchese laid claim to it.

What the town adds up to is a settlement built in tiers: a prehistoric mountain, a contested medieval center, and a Renaissance overlay that reorganized the base of the hill without touching what stood above it.

The re-enactment here is Corsa delle brocche a Cetona, usually held in July.

What to see in Cetona

• Piazza Garibaldi. Elliptical square at the foot of the medieval grid, flat and open where the streets above it climb steeply. The civic stage of the borgo, still the first thing that orients a visitor.
• Rocca di Cetona. Fortress at the top of the centro storico, its walls and keep still standing though the interior became a private residence rather than a garrison.
• Convento di San Francesco. Franciscan convent below the borgo, founded in 1212, with a single-nave church and a small cloister still in religious use.

How to get to Cetona

There is no station we could confirm here, so this one means driving. Perugia is roughly 78 minutes away by road.

Everything we know about Cetona

Bevagna

Why visit Bevagna

Bevagna sits on the floor of the Umbrian valley at 225 meters, where the Clitunno meets the Timia. Ancient Mevania, the name means she who stands in the middle, was a Roman mansio on the Via Flaminia, listed in the Antonine Itinerary.

A black-and-white mosaic of the 2nd century AD survives almost intact in the frigidarium of the Roman baths, twelve meters by seven, octopuses and dolphins in the center, tritons and sea-horses on the short sides. Piazza Silvestri at the heart of the centro storico holds two Romanesque churches that face each other at odd angles, San Michele Arcangelo and San Silvestro, built within years of each other in the late 12th century.

The Mercato delle Gaite each June turns the town into the year 1300 for ten days, four quarters competing on medieval trades and tavern menus, no anachronisms allowed. The Sagrantino slopes of Montefalco are nine kilometers up the road.

The re-enactment here is La Notte Medievale, usually held in September.

What to see in Bevagna

• Piazza Silvestri. Twelfth-century civic square ringed by the Palazzo dei Consoli, the churches of San Silvestro and San Michele, and the fountain of 1896.
• Chiesa di San Michele Arcangelo. Romanesque collegiate church built by Binello and Rodolfo at the end of the 12th century, on the main square.
• Chiesa di San Silvestro. Romanesque parish church across the piazza, signed and dated 1195 by Binello, the same builder as San Michele.

How to get to Bevagna

There is no station we could confirm here, so this one means driving. Perugia is roughly 39 minutes away by road.

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Anghiari

Why visit Anghiari

Anghiari sits at 430 meters on a spur above the upper Tiber valley, the Valtiberina, between Arezzo and the Umbrian border. The walled centro storico is intact, the streets running steeply from the Porta Sant'Angelo up to the Castello.

On 29 June 1440 the Florentine army defeated a Milanese force under Niccolò Piccinino in the plain below town, a battle that secured Florence's hold over central Italy and gave Leonardo da Vinci the commission for the Palazzo Vecchio fresco he started in 1505 and never finished. The painting, the Lost Leonardo, is presumed still to be hidden behind a Vasari wall in Florence.

Palazzo Taglieschi in the centro storico holds a polychrome wooden Madonna by Jacopo della Quercia and a working sixteenth-century table organ. The Mostra Mercato dell'Artigianato della Valtiberina has filled the streets with craft producers every spring since 1976, a working continuation of the textile and woodwork traditions that supported the town through the twentieth century.

The re-enactment here is Palio della Vittoria di Anghiari, usually held in June.

What to see in Anghiari

• Palazzo Taglieschi. Sixteenth-century palace in the centro storico, now the Museo Statale di Palazzo Taglieschi, with a wooden Madonna by Jacopo della Quercia and a working table organ.
• Castello di Anghiari. Medieval fortified core at the top of the town, walls and gates still intact, the visual anchor of the silhouette from the valley below.
• Campo della Battaglia. The plain at the foot of the walls where Florence defeated Milan on 29 June 1440, the battle that inspired Leonardo's lost Palazzo Vecchio fresco.

How to get to Anghiari

There is no station we could confirm here, so this one means driving. Perugia is roughly 82 minutes away by road.

Everything we know about Anghiari

Nocera Umbra

Why visit Nocera Umbra

Nocera Umbra sits fifteen kilometers north of Foligno. The Romans called it Nuceria; the town has held its own bishopric since the early Middle Ages and was contested between Perugia, Spoleto and the Trinci of Foligno through the medieval period, a tug of war between larger powers that left it walled and defensible on its slope rather than absorbed by any one of them.

The centro storico climbs to a summit where the tower, the cathedral and the former Rocca stand together, the civic and the religious and the military crowded onto the same high ground. Below, five kilometers down from that core, the springs form a separate pole of the town's life, functional rather than defensive, drawing visitors for water rather than for stone.

The Bandiera Arancione recognition was reconfirmed after reconstruction, a marker that the rebuilding did not just replace what fell but held the town to the standard it met before the quake.

The re-enactment here is Palio dei Quartieri, usually held in August.

What to see in Nocera Umbra

• Campanaccio (Torre Civica). Eleventh-century square tower at the highest point of the borgo. Only part of one side remained standing after 1997; the rest is reconstruction, stone matched to stone.
• Pinacoteca e Museo Civico. Civic gallery in the deconsecrated Chiesa di San Francesco with works by Niccolò Alunno, Matteo da Gualdo, and the school of Cimabue.
• Cattedrale di Santa Maria Assunta. Cathedral at the summit of the centro storico, partially damaged and restored, set beside the tower and the former Rocca.

How to get to Nocera Umbra

There is a railway station in the town, so you can arrive without a car and never need one while you are here. Perugia is roughly 57 minutes away by road.

Everything we know about Nocera Umbra

Sassoferrato

Why visit Sassoferrato

Sassoferrato sits on the eastern slope of the Apennines on two levels: the Borgo at around 310 meters and the Castello at 400 meters, dominated by the Rocca built in 1365 by order of Cardinal Albornoz. A kilometer south of the modern town lies Sentinum, the Roman city next to which the consuls Publius Decius Mus and Fabius Maximus Rullianus defeated a coalition of Samnites, Etruscans, Umbrians and Senone Gauls in 295 BC, in the decisive battle of the Third Samnite War that allowed Rome to unify central Italy.

The archaeological park preserves the cardo and decumanus, the urban baths, a second extramural bath complex and the ruins of a metalworking shop. The Civic Archaeological Museum inside the Palazzo dei Priori, built 1355, holds the finds from Sentinum, including a Byzantine Saint Demetrius mosaic icon on wooden support.

Giovanni Battista Salvi, called Il Sassoferrato, was born here in 1609; Palazzo Oliva holds a collection of his Raphaelesque devotional paintings. The town gives its name to the Battle of the Nations historical reenactment, held each August.

The re-enactment here is Palio della Miniera di Zolfo, usually held in August.

What to see in Sassoferrato

• Rocca Albornoz. Fourteenth-century fortress built 1365 by order of Cardinal Albornoz, dominating the upper Castello district at 400 meters.
• Parco Archeologico di Sentinum. Roman city a kilometer south of town, with the cardo and decumanus, the urban baths and the extramural bath complex still visible.
• Museo Civico Archeologico. Inside the 1355 Palazzo dei Priori, holding the finds from Sentinum and the Byzantine Saint Demetrius mosaic icon on wooden support.

How to get to Sassoferrato

There is no station we could confirm here, so this one means driving. Perugia is roughly 74 minutes away by road.

Everything we know about Sassoferrato

Città della Pieve

Why visit Città della Pieve

Città della Pieve sits on a hill at 508 meters between Umbria and Tuscany, about 260 meters above the Valdichiana and within sight of Lake Trasimeno. The town is built almost entirely of the local red brick that has been fired here since the Middle Ages, which gives the centro storico a uniform terracotta color.

Pietro Vannucci, known as Perugino, was born here around 1448 and returned in 1504 to fresco the Adoration of the Magi inside the Oratorio di Santa Maria dei Bianchi, one of the largest works he ever painted. The Cathedral of San Gervasio holds two more Perugino panels from 1510 and 1514.

Pope Clement VIII elevated the town from Castel della Pieve in 1600, restoring its episcopal seat. Vicolo Baciadonne, eighty centimeters wide, threads between two brick walls and is regularly cited as the narrowest alley in Italy.

The re-enactment here is Palio dei Terzieri, usually held in August.

What to see in Città della Pieve

• Cattedrale dei Santi Gervasio e Protasio. Cathedral on the main piazza with two Perugino panels, the Madonna and Child with Saints of 1514 and the Baptism of Christ of 1510.
• Oratorio di Santa Maria dei Bianchi. Confraternity oratory holding Perugino's Adoration of the Magi, frescoed in 1504 and considered one of his largest single works.
• Torre del Pubblico. Twelfth-century civic tower in Lombard Romanesque style, thirty-nine meters tall, set next to the cathedral on Piazza Plebiscito.

How to get to Città della Pieve

There is a railway station in the town, so you can arrive without a car and never need one while you are here. Perugia is roughly 47 minutes away by road.

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Chiusi

Why visit Chiusi

The hilltop stands above the Val di Chiana, the valley floor visible from the town at a height that made it defensible and gave it command of the surrounding farmland. The cathedral, the museums and the tunnel network are close enough to walk between within the old center, while the painted necropolis and the lake lie outside it, a few kilometers apart in different directions, one inland toward the tombs and the other north toward open water.

The tunnels themselves connect the upper town to what lies beneath it: built as drainage, later folded into legend by Pliny the Elder, who took them for part of a king's tomb. The cathedral's own columns, lifted from earlier Roman buildings, make the same point in stone that the tombs make in paint and the museum makes in bucchero and alabaster: this is a town built repeatedly on top of itself, each layer reusing what the last one left behind.

The re-enactment here is Tria Turris Medioevo e Palio delle Torri di Chiusi, usually held in June.

What to see in Chiusi

• Museo Nazionale Etrusco. Holds canopic urns, alabaster sarcophagi, bucchero pottery and grave goods pulled from the necropolises around the town.
• Duomo di San Secondiano. Cathedral built around 560 AD over an earlier basilica, renovated in the thirteenth century, nave and two aisles on antique marble columns from Roman buildings.
• Labirinto di Porsenna. Visited from the Museo della Cattedrale, the tunnels run beneath the streets at a scale that still reads as engineering rather than legend, whatever Pliny made of them.

How to get to Chiusi

There is a railway station in the town, so you can arrive without a car and never need one while you are here. Perugia is roughly 58 minutes away by road.

Everything we know about Chiusi

Deruta

Why visit Deruta

Deruta sits fifteen kilometers south of Perugia, its hill rising above the Tiber on the river's left bank. The walled medieval core, organized around Piazza dei Consoli, occupies the high ground, while the lower town spreads along the old road linking Perugia to Rome.

That road is where the workshops cluster, most of them family businesses running three or four generations deep, and it is also the route that carries traffic five kilometers south to the pilgrimage church, its walls built up over four centuries from votive tiles left by travelers on the same stretch of road. The first documented kilns appear in the archaeological record in the late thirteenth century, and by the early sixteenth the town's workshops had developed the lustro finish that gave Deruta wares their metallic shine, along with the Bella Donna plates that paired painted portraits with flattering banderoles naming the women depicted.

That convent complex, once a working monastery, now holds both the ceramics museum and, next door, the civic gallery with its Perugino and Alunno panels, so the town's religious architecture, its art collection, and its ceramics history sit under the same roof by accident of reuse rather than design. The upper town's churches and museums hold the record of what Deruta made and believed; the lower town's workshops are still making it.

The re-enactment here is Palio della Brocca, usually held across August and September.

What to see in Deruta

• Museo Regionale della Ceramica. Holds over 6,000 pieces from medieval to modern, arranged through the convent's old cloister and cells.
• Chiesa di San Francesco. Consecrated 1388 after earthquake reconstruction, Sienese 14th-century frescoes inside, Domenico Alfani Raphael-school panel above an altar.
• Pinacoteca Comunale. Civic gallery with Perugino's Eterno and Saints Romano e Rocco, plus two altarpieces by Niccolò Alunno from the surrounding churches.

How to get to Deruta

There is a railway station in the town, so you can arrive without a car and never need one while you are here. Perugia is roughly 19 minutes away by road.

Everything we know about Deruta

Castiglion Fiorentino

Why visit Castiglion Fiorentino

The hill stands between Arezzo and Cortona, above the fertile plain that gives the area its name. The centro storico is layered directly on what came before it: the medieval streets and the fortress at the summit sit on foundations from the fourth century BC, so walking from the lower gates to the top of the town is also a climb through the town's own construction history, one period built on the next rather than beside it.

The upper terrace holds the oldest religious building along with the fortress, while the main piazza lower down gathers the later additions, the parish church, the arcade, and the gallery, into a single civic space. The town carried allegiance first to Perugia, then to Florence from 1384, and was renamed at that moment, a change of name that marks the point where the additions to the skyline, the arcade among them, became possible.

What results is a town where the sightlines do the explaining: the arcade frames the plain because the plain was always the reason to build here, and the fortress crowns the hill because it was already fortified ground long before anyone called it that.

The re-enactment here is Palio dei Rioni di Castiglion Fiorentino (Arezzo), usually held in June.

What to see in Castiglion Fiorentino

• Cassero. Fortified core at the top of the town. The tower is reached by climbing through the streets of the centro storico, with the drop toward the plain opening out only at the top.
• Logge del Vasari. The three arches sit at the edge of Piazza del Municipio, so the arcade functions as a frame for the view rather than a monument to walk around. Below it, the Pinacoteca occupies the neighboring building.
• Pinacoteca Comunale. Civic gallery next to the Logge with works by Bartolomeo della Gatta, Margaritone d'Arezzo, Taddeo Gaddi and a notable bust reliquary in gilded silver.

How to get to Castiglion Fiorentino

There is a railway station in the town, so you can arrive without a car and never need one while you are here. Perugia is roughly 54 minutes away by road.

Everything we know about Castiglion Fiorentino

Montepulciano

Why visit Montepulciano

The ridge runs between the Val di Chiana and the Val d'Orcia, 70 kilometers southeast of Siena, and the town follows its spine uphill: streets climb from the gates toward the high point, where the main square sits ringed by the buildings that define the skyline from below. The origin predates the Renaissance fabric by centuries.

Etruscan tombs survive in the surrounding hills, though almost nothing of that period shows in the centro storico itself, which was rebuilt wholesale in the fifteenth and sixteenth centuries over whatever came before. The wine and the festival both use the climb as their setting rather than their subject: the cellars are cut into the rock beneath the palazzi, keeping a constant temperature for aging, and the barrel race each August sends two men from each of the eight contrade hauling an eighty-kilogram cask up the same gradient that every visitor covers on foot, only slower.

The steepness that shaped the defensive site nine centuries ago is still what a person feels first, in the legs, before the buildings register at all.

The re-enactment here is Bravio delle Botti, usually held in August.

What to see in Montepulciano

• Tempio di San Biagio. A 13-meter dome and travertine façade standing alone outside the walls, the ground falling away below it so the building reads as a single volume against the hillside.
• Piazza Grande. The high piazza at the top of the ridge, ringed by the Duomo, the Palazzo Comunale and the Palazzo Tarugi, all rebuilt in the fifteenth and sixteenth centuries.
• Palazzo Comunale. Town hall designed by Michelozzo in the fifteenth century, its tower offering a view over the Val di Chiana and Val d'Orcia.

How to get to Montepulciano

There is a railway station in the town, so you can arrive without a car and never need one while you are here. Perugia is roughly 57 minutes away by road.

Everything we know about Montepulciano