The best hidden towns with a food festival that have a serious restaurant in Toscana
Tuscany eats by the calendar. The oil comes down green and peppery in November and the mills run late; the truffle season turns the crete senesi damp and profitable; boar arrives after the hunt, cooked long with juniper and red wine. In the towns themselves this shows up as a sagra, a food festival with trestle tables under a loggia of pietra serena or brick, a paper plate of pici, and a queue that includes the mayor. What is unusual about these particular towns is that the sagra is not the only food worth planning around, because each also keeps a restaurant that the most demanding of the guides has been to and rated.
the second thing everyone knows about Tuscan food is Florence, and Florence deserves it: the Mercato Centrale, the bistecca, the wine windows reopened for spritzes. In practice this means booking weeks out for a table, eating at half past seven with everyone else who booked weeks out, and paying city prices for produce grown two hours south. Siena in Palio season and the Chianti wine road between them absorb most of the rest, so the same handful of streets carries the reputation of an entire region.
The ingredient does not stop at the city limits. The oil presses, the boar, the pecorino and the lagoon eels are all somewhere else, in the Val d'Orcia and the Maremma, in the Casentino above Arezzo and the hills around Chiusi and Cetona, and the festivals happen where the food is grown rather than where it is sold. Fewer people go, tables are easier, and the cooking has a shorter distance to travel. These are those towns.
Of the 84 communes we have mapped in Toscana, 14 qualify as towns with a food festival with a serious restaurant: each holds a recurring food festival built around one local ingredient, and each holds a restaurant listed by the most demanding of the guides. This list is the hidden ones, 10 in all, ordered smallest first. The smallest, San Casciano dei Bagni, has 1,500 residents.
If you are still choosing, we have also written The best hidden towns with a medieval festival in the province of Siena and The best towns with a food festival in the province of Siena.
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.
Daniela, Castello di Fighine have been named by a guide.
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.
Da Nilo, Il Tiglio di Piazza da Nilo have been named by a guide.
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.
Poppi
Why visit Poppi
Poppi rises above the upper Arno in the Casentino, the wooded valley set between Pratovecchio and Bibbiena. The Counts Guidi held this hill from at least 1169, and the castle they raised across the late twelfth and thirteenth centuries is attributed in its older part to Lapo di Cambio and in the later upper section to Arnolfo di Cambio.
Dante Alighieri, who fought below the hill as a young man, returned to it later as a guest of the Guidi during his exile, so the borgo held him twice, once as a soldier and once as a household guest. The town itself sits above the battle plain, the abbey church inside the walls, the castle over both.
A further Romanesque pieve stands a short distance off, and the forested ridges of the Apennine watershed rise to the east, the same terrain the Guidi once ruled from their hill. What the place adds up to is a single family's hold on a valley, visible still in the line from castle to plain to church, with the forest marking where their lordship ran out.
Il Cedro, Mater have been named by a guide.
What to see in Poppi
- Castello dei Conti Guidi. The castle keeps a working library and a fourteenth-century chapel frescoed by the school of Giotto, along with a hand-painted model of the battle below, more than four thousand tin soldiers set out on the table.
- Piano di Campaldino. The plain sits directly beneath the castle walls, open ground still readable as a battlefield, with nothing built across it since.
- Abbazia di San Fedele. Romanesque abbey church inside the borgo, with single nave and stone façade, dating from the early twelfth century.
How to get to Poppi
There is a railway station in the town, so you can arrive without a car and never need one while you are here. Firenze is roughly 64 minutes away by road.
Our tip
April through June brings the Casentino into clear sun, the beech forests in their first leaf and the upper Arno full from spring rain. July and August are pleasant at 437 meters, never coastal-hot, with the castle and library full of weekend visitors from Florence. September and October are the harvest and chestnut months: the Foreste Casentinesi turn orange in the high cuts above Pratovecchio. Il Casentino nel piatto falls in June.
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.
Trattoria Toscana al Vecchio Forno, Da Ciacco have been named by a guide.
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.
✷ We have written about San Quirico d'Orcia
“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 San Quirico d'Orcia →Val d'Orcia | The Postcard Is Constructed
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.
Caffè Fiaschetteria Italiana, Campo del Drago, La Sala dei Grappoli and 13 more have been named by a guide.
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.
Castiglione della Pescaia
Why visit Castiglione della Pescaia
Castiglione della Pescaia sits at sea level on the Maremma coast, north of Grosseto, with a medieval upper town rising on the promontory above the harbor. The site was Roman Salebrone, before that Etruscan and Umbrian, settled because of the lake behind it that the Romans called Portus Traianus.
The lake silted up over time; what remains of it is the wetland reserve southeast of town, a Ramsar site since 1991. The upper town and the harbor below it read as two halves of one settlement: the fortress watching the water from above, the working port beneath, and behind both the flat reclaimed ground where the lake used to be.
Inland and to the east, the hills hold the remains of one of the major Etruscan cities, apart from the coastal life below. North of town, the pine forest gave Calvino his summers and now holds his grave on the hill above the harbor.
The place is built in layers: a silted lake turned nature reserve, a watchtower turned fortress, an Etruscan hill city, and a modern coastline still shaped by all of it.
La Trattoria Enrico Bartolini, Osteria del Mare già il Votapentole, Clann and 1 more have been named by a guide.
What to see in Castiglione della Pescaia
- Rocca Aragonese. Castle on the promontory above the harbor, 10th-century watchtower core enlarged by Alfonso of Aragon in the 15th century, modified by Cosimo I and the Lorraine.
- Riserva Naturale Diaccia Botrona. Wetland reserve southeast of town with bird-watching hides, pink flamingos and white herons in season.
- Casa Rossa Ximenes. Hydraulic structure built by Jesuit engineer Leonardo Ximenes for the Lorraine drainage works; now multimedia museum of the wetland reserve.
How to get to Castiglione della Pescaia
There is no station we could confirm here, so this one means driving. Livorno is roughly 113 minutes away by road.
✷ We have written about Castiglione della Pescaia
“Everyone driving from Florence down to Rome crosses the Maremma without noticing, because there is nothing on that stretch to make them slow down. The hills give out. The cypresses stop. What opens up instead is flat open country, wheat and grass running off to a few low rises, the least Tuscan-looking part of Tuscany, a landscape you would call dull if you were being honest and which most guidebooks solve by leaving out.”
Read our piece on Castiglione della Pescaia →Maremma | The Last Cowboys of Tuscany
Our tip
May and June bring warm sea and quiet beaches, before the high-summer crowds arrive from Rome and Florence. June through September holds the Bandiera Blu and the Diaccia Botrona stays accessible in the cooler hours. July and August push the coast above thirty; Punta Ala and the harbor fill, and the Rocca above the old town becomes a sunset destination. Palio Marinaro di Castiglione della Pescaia falls in August.
Volterra
Why visit Volterra
Volterra sits at 531 meters on a long ridge between the Era and Cecina valleys, one of the twelve cities of the Etruscan dodecapolis and the only one still occupied on its original ground. The Etruscans called it Velathri, the Romans Volaterrae; the Porta all'Arco, with three blackened tufa heads of unknown deities, has been the western gate of the town since the fourth century BC.
The Roman theater below the walls, excavated in the 1950s, holds two complete rows of columns and the bath complex behind the stage. Above stands the Palazzo dei Priori, begun in 1208 and the oldest town hall in Tuscany, the model for Florence's Palazzo Vecchio.
The town has been carving alabaster since the Etruscans, who used it for funerary urns; the same workshops on Via Porta all'Arco still cut and polish the soft white stone today. Le Balze, the eroded clay cliffs west of town, swallow a few meters of churchyard every century.
Villa Pignano, Enoteca Del Duca have been named by a guide.
What to see in Volterra
- Porta all'Arco. Etruscan city gate from the fourth century BC, with three eroded tufa heads of unknown deities set above the arch.
- Teatro Romano. First-century BC Roman theater excavated in the 1950s, with two complete rows of columns and the bath complex behind the stage.
- Palazzo dei Priori. Begun in 1208, the oldest town hall in Tuscany, the architectural model for Florence's Palazzo Vecchio.
How to get to Volterra
There is no station we could confirm here, so this one means driving. Livorno is roughly 83 minutes away by road.
✷ We have written about Volterra
“The wine is the whole economy of these hills, every village with its own, the region’s name stamped on the most famous red in Italy. Tuscan food runs to cured and roasted meat, so the wine ran red to meet it, lighter than you expect, almost fruity, easy, made to sit beside a steak and not to be lectured about. Here is the only wine knowledge you need on this road: it is all good.”
Read our piece on Volterra →Road to Siena | The Long Way Is the Better Way
Our tip
April through June brings the surrounding clay hills green and the temperatures bearable on the exposed ridge. September and October are the second window, with the white truffle harvest peaking at Volterragusto in late October. July and August are hot and bright at altitude; the town fills with Italian and foreign visitors, and the Etruscan urns at the Guarnacci feel cool by comparison. Mostra Mercato del Tartufo Marzuolo falls in April.
Orbetello
Why visit Orbetello
The isthmus runs out into the lagoon and splits it into two basins, Ponente and Levante. Two sand tombolos close the shape from either side: Giannella to the north, Feniglia to the south, both reaching toward the Monte Argentario promontory and meeting it at either end.
The Etruscans settled the site first, the Romans followed with their colony of Cosa nearby, and centuries later the Spanish took the isthmus as the seat of their coastal enclave, leaving the Governor's Palace on the main square where it still stands. Of the nine Sienese windmills once built out in the water, one remains in place, the only Italian water-and-wind mill of its type still fixed where it was built.
The lagoon that once carried Balbo's flying boats out toward Rio and Chicago now carries a WWF reserve and the nets of a bottarga and eel cooperative working the same waters since 1965. A town built on the water it is named for, held between two arms of sand and one mountain it never quite touches.
L'Oste Dispensa, Osteria Bolle have been named by a guide.
What to see in Orbetello
- Duomo di Santa Maria Assunta. Fourteenth-century cathedral with a Gothic travertine façade, rebuilt over an earlier Etruscan-Roman temple foundation.
- Fortificazioni Spagnole. The bastions and the Polveriera Guzman magazine, still standing along the edges of the historic center.
- Laguna di Orbetello. The brackish water splits into two basins and is now a WWF reserve and Ramsar wetland.
How to get to Orbetello
There is a railway station in the town, so you can arrive without a car and never need one while you are here. Roma is roughly 124 minutes away by road.
Our tip
May through September is when the lagoon and the Feniglia and Giannella beaches do their work. June brings the migratory bird count back up: flamingos, herons, avocets. July and August push temperatures over thirty degrees and the tombolos fill with Roman day-trippers, so the lagoon path on the Ponente side stays the quieter option. Sagra del Pesce di Albinia 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.
I Salotti, Il Grillo è Buoncantore, La Solita Zuppa have been named by a guide.
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.
Ristorante Caffè Pasticceria Poliziano, Osmosi, Le Logge del Vignola and 3 more have been named by a guide.
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.
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