The best towns with a food festival in the province of Siena
Autumn in the province of Siena smells of woodsmoke, wet oak leaves and pork fat hitting a grill in a piazza built of travertine and warm brick. This is where the sagra still does its original work: a town clears its main square, sets up trestle tables, and cooks the one thing it grows better than its neighbours. Pecorino from the Val d'Orcia, chestnut flour ground on the flanks of Monte Amiata, white truffle from the woods above the Val di Chiana, hand-rolled pici under a sauce of garlic and tomato, Sangiovese poured from unlabelled bottles. Spring and early summer bring the artichoke and the broad bean; late summer brings the grape harvest and the first porcini.
Most visitors to this landscape spend their days in Siena, on the Campo and up the Torre del Mangia, then drive out for a sunset photograph of a cypress avenue. The city earns the attention, and the Palio concentrates it further, filling every room within an hour's radius twice each summer. The result is that the province is largely seen from a coach window between the walls and the airport, and the food is eaten in restaurants priced for people who will not come back.
The same hills carry on south and east past all that, into the Val d'Orcia, the Val di Chiana, the crater lakes and the volcanic slopes of the Amiata. The towns there keep their festival calendars for their own reasons, which is why the tables are long, communal and cheap, and why the cook is usually somebody's aunt. These are the smaller places, and fewer people go.
Of the 20 communes we have mapped in the province of Siena, 8 qualify as towns with a food festival: each holds a recurring food festival built around one local ingredient. The smallest, San Casciano dei Bagni, has 1,500 residents.
Elsewhere in the catalogue: The best hidden towns with a medieval festival in the province of Siena and The best hidden towns with a food festival that have a serious restaurant in Toscana.
San Casciano dei Bagni
Why visit San Casciano dei Bagni
San Casciano dei Bagni sits at 582 meters at the southern edge of the province of Siena, above 42 hot springs that average 42 degrees Celsius. The baths were used continuously from Etruscan through Roman times and again from the Renaissance, when visitors came from across Europe.
In 2022, an excavation that began in 2019 at the ancient sanctuary turned up 24 bronze votive statues protected by mud, with around 6,000 coins in gold, silver and bronze. The find was the largest of its kind in fifty years; most surviving Etruscan votive material is terracotta.
The 1,500 residents live on a basalt outcrop above the Roman thermal complex, in a centro storico of stone houses and three small churches. The borgo joined the Borghi più belli network in 2014 and remains one of the smallest communes in Toscana to carry both that label and Bandiera Arancione.
The re-enactment here is Palio di San Cassiano di San Casciano dei Bagni, usually held in August.
What to see in San Casciano dei Bagni
- Santuario Ritrovato. Etruscan-Roman thermal sanctuary excavated since 2019, where 24 bronze votives and around 6,000 coins were recovered in 2022.
- Bagno Grande. The principal natural pool of the 42 hot springs, used from the second century BC through the Renaissance and reopened to the public.
- Collegiata di San Leonardo. Romanesque parish church in the centro storico, restored in the seventeenth century, with a baptismal font carved from local travertine.
How to get to San Casciano dei Bagni
There is no station we could confirm here, so this one means driving. Perugia is roughly 68 minutes away by road.
Our tip
The thermal pools make the calendar different here. Winter is the season many visitors prefer, when the 42-degree water steams against cold air and snow occasionally dusts the basalt outcrop. April through June and September into October are the most balanced months: warm hill light, the dry-stone walls of the borgo at their best, the sanctuary excavations open to guided tours. Sagra del Ciaffagnone di San Casciano dei Bagni falls in June.
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.
Our tip
April through June and September into October are the months Cetona keeps its calmest pace, the wooded slopes of Monte Cetona green or rust depending on the half. July and August are hot in the centro storico but the mountain trails above 800 meters stay cool. The Mostra del Tartufo, dedicated to the local white truffles, runs the second weekend of November in Piazza Garibaldi. Sagra del Bico di Cetona falls in June.
Piancastagnaio
Why visit Piancastagnaio
The name means plain of the chestnut, and the forest that still climbs the slope above the town is what fed it for most of its history: sweet chestnut, sessile oak, beech. The town itself sits at 772 meters, built around a twelfth-century keep that passed to Siena in 1418 and to the Medici in 1559, and the palazzo built into its old defenses in the sixteenth century reads as the Medici layer set directly against the Aldobrandeschi one.
Contrade named Borgo, Castello, Coro and Voltaia divide the centro storico for the August race, while the mining museum keeps the record of an industry, cinnabar and mercury, that ran on the mountain from Etruscan times until it closed in 1982 and that has otherwise left the town to the chestnut trade. What Piancastagnaio adds up to is a place where a volcano's slope has supplied, in turn, timber and food, ore, and a festival calendar, and where the built town still carries each of those histories as a separate, legible layer rather than a single blended one.
The re-enactment here is Palio delle Contrade di Piancastagnaio, usually held in August.
What to see in Piancastagnaio
- Rocca Aldobrandesca. Twelfth-century Aldobrandeschi keep at the heart of the centro storico, with a square tower and surviving curtain wall.
- Palazzo Bourbon del Monte. Sixteenth-century Medici-era palazzo built into the medieval defenses, with a courtyard loggia and ceremonial hall.
- Museo Minerario di Sant'Anna. Mining museum on the cinnabar and mercury extraction of Monte Amiata, active from the Etruscans until the mine closed in 1982.
How to get to Piancastagnaio
There is no station we could confirm here, so this one means driving. Perugia is roughly 135 minutes away by road.
Our tip
May through September is the season on the southern Amiata slope. The chestnut woods are open, the air at 772 meters stays cool against the Maremma heat below, and the trails to the volcano summit run from town. The Palio delle Contrade is the second weekend in August, the only date most outsiders know. Crastatone di Piancastagnaio falls in the season.
Pienza
Why visit Pienza
Pienza sits at 491 meters on a long ridge in the Val d'Orcia, an hour and a half south of Siena. The village was called Corsignano until 1462.
Enea Silvio Piccolomini was born here in 1405 and became Pope Pius II in 1458; the following year he ordered the Florentine architect Bernardo Rossellino to rebuild his birthplace as a Renaissance ideal city. The work took three years.
The square at the center, the cathedral on the cliff side, the palace built for the pope's family, the cardinal's palace facing it, and the town hall opposite the cathedral were all designed and built as a single composition rather than assembled piece by piece over time. Pius consecrated the cathedral on 29 August 1462, two years before his death, and the whole arrangement has survived almost unchanged since.
What stands in Pienza today is less a collection of monuments than the physical record of one commission carried out in one stretch of years.
What to see in Pienza
- Piazza Pio II. Trapezoidal Renaissance square laid out by Bernardo Rossellino, with the Duomo, Palazzo Piccolomini, Palazzo Borgia and Palazzo Comunale facing each other.
- Duomo di Pienza. Latin-cross cathedral with three apsidal chapels, built on the cliff edge, its Renaissance façade also by Rossellino.
- Palazzo Piccolomini. Renaissance palace for the pope's family, begun 1459, with an internal courtyard and a hanging garden overlooking the Val d'Orcia.
How to get to Pienza
There is no station we could confirm here, so this one means driving. Perugia is roughly 98 minutes away by road.
✷ We have written about Pienza
“When the film industry needed a picture of heaven, of the fields a dead hero walks home to, they came and shot it here, and that is the truest thing anyone has ever said about the Val d'Orcia. It is not a place. It is the afterlife as imagined by people who lived in cities. It is how the country looks to men who never spent an hour in it, dreamed up by Florentine bankers five hundred years ago and maintained, beautifully, ever since.”
Read our piece on Pienza →Val d'Orcia | The Postcard Is Constructed
Our tip
April through June and September into October are the months when the Val d'Orcia sits at its best, green or gold depending on the wheat cycle, and the Piazza Pio II is open for photographs without the day-tripper buses. July and August push past thirty-three degrees and the Corso Rossellino fills with tour groups between ten and four. The Fiera del Cacio, the cheese festival, takes the first Sunday in September, when the streets fill with stalls of pecorino producers from the Pienza ridge. Festa del Cacio di Pienza falls in September.
San Quirico d'Orcia
Why visit San Quirico d'Orcia
San Quirico d'Orcia sits at 409 meters on a low rise in the Val d'Orcia, the rolling clay-and-tufa landscape inscribed by UNESCO in 2004 as a cultural landscape shaped by fourteenth and fifteenth-century Sienese governance. The town was a stage on Sigeric the Serious's tenth-century Via Francigena from Canterbury to Rome and has remained a working stop on the route ever since.
The Collegiata dei Santi Quirico e Giulitta was built at the end of the twelfth century over an eighth-century baptistery; the lateral portal added in 1288 is attributed to Giovanni Pisano, then working on the Siena cathedral. The Horti Leonini, the geometric boxwood garden laid out by Diomede Leoni around 1580 inside the town walls, hosts the Forme nel Verde sculpture exhibition every summer since 1971.
Bagno Vignoni, the frazione five kilometers down the road, has a thermal pool at the center of its piazza, used since Etruscan times. Few comuni this small carry UNESCO, thermal and Francigena signals at once.
The re-enactment here is Festa del Barbarossa a San Quirico d'Orcia, usually held in June.
What to see in San Quirico d'Orcia
- Collegiata dei Santi Quirico e Giulitta. Romanesque parish church built late twelfth century over an eighth-century baptistery, with the 1288 lateral portal attributed to Giovanni Pisano.
- Horti Leonini. Italianate boxwood garden laid out by Diomede Leoni around 1580 inside the town walls, hosting the Forme nel Verde sculpture exhibition since 1971.
- Bagno Vignoni. Frazione five kilometers south, with a sixteenth-century thermal pool at the center of its piazza, fed by springs used since Etruscan times.
How to get to San Quirico d'Orcia
There is no station we could confirm here, so this one means driving. Perugia is roughly 96 minutes away by road.
Our tip
April through June and September into October are the gold months in the Val d'Orcia: green wheat in spring, ochre stubble by autumn, low light that defines the cypress ridges. The Festa del Barbarossa runs the third Sunday of June with archery, jousts and crossbow contests between the town quarters. July and August are hot and busy; the centro storico fills with day-trippers from Pienza and Montalcino. Festa del Barbarossa a San Quirico d'Orcia falls in June.
Montalcino
Why visit Montalcino
Montalcino sits at 564 meters on a hill south of Siena, the centro storico ringed by walls and crowned by a pentagonal fortress built in 1361. When Florence took Siena in 1555, the Sienese exiles regrouped here and held out for almost four years; the Rocca itself never fell.
That date matters less to most visitors than 1980, when Brunello di Montalcino was named one of the first four Italian wines to receive DOCG status. The vineyards run from the town at 600 meters down to plots at 200, on stony galestro soils that ripen Sangiovese Grosso into a wine that ages for decades.
The Abbey of Sant'Antimo, ten kilometers south, is a Romanesque church first documented in 814 and tied by local legend to a vow by Charlemagne. The town also produces miele, olio, and the white truffles of the surrounding woods.
It carries seven institutional signals at once, more than any other commune in this batch.
The re-enactment here is Torneo di Apertura delle Cacce a Montalcino, usually held in August.
What to see in Montalcino
- Rocca di Montalcino. Pentagonal fortress built in 1361 by Sienese architects Mino Foresi and Domenico di Feo, refuge of the Sienese Republic after 1555.
- Abbazia di Sant'Antimo. Romanesque abbey ten kilometers south, first documented in 814, set among olive groves below the town with Gregorian chant still sung.
- Palazzo dei Priori. Thirteenth-century town hall on Piazza del Popolo, slender tower attached, civic seat of the medieval commune.
How to get to Montalcino
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 105 minutes away by road.
Our tip
April through June and September into October are the months locals prefer. The hills are green or gold depending on the half, and the vineyards run their full work cycle. The Sagra del Tordo, a medieval archery contest between the four quarters of the town, takes place the last Sunday of October. Sagra del Cinghiale di Montalcino falls in the season.
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.
Our tip
April through June and September into October are the working months on the Val di Chiana edge: mild days, evening light over the lake, the wine and olive cycles below town. The Frittellata of San Giuseppe in mid-March and the Festa di San Mustiola in early June fill the centro storico with traditional kitchens. July and August push past thirty degrees and the basin below town holds the heat; the museums and the Labirinto stay cool. Tria Turris Medioevo e Palio delle Torri di Chiusi falls in June.
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.
Our tip
April through June and September into October are the working months on the ridge: vine work in the surrounding hills, mild days, evening light that lingers over the Val d'Orcia. July and August push into the low thirties and the climb to Piazza Grande slows even the residents. The Bravìo delle Botti runs the last Sunday of August and fills the town. Calici di Stelle falls in July.
More from Anywhere Italy
- The best hidden towns with a medieval festival in the province of Siena
- The best hidden towns with a food festival that have a serious restaurant in Toscana
The best small towns with a food festival in Toscana- The best wine towns with a food festival in Toscana
- The best hidden wine towns with a medieval festival in Toscana
The best small olive oil towns in the province of Siena