The 7 prettiest villages with a food festival in Toscana
Autumn is when Tuscany stops performing and starts cooking. Chestnuts are roasted in perforated pans over vine cuttings, the year's oil comes out of the mill green and peppery and gets poured over toasted bread in the street, and village squares of sandstone and travertine fill with trestle tables. The villages themselves are built from what the hillside gave up: pietra serena around the doorways, roofs of curved terracotta gone grey with lichen, plaster the colour of dried clay. Spring and early summer bring their own festivals, artichokes, cherries, wild asparagus, snails, but the calendar tilts heavily towards the months after harvest.
Most people arrive for Florence and Siena, and in high season the queue for the Uffizi bends around the building while Piazza del Campo takes the full weight of the coach parks. The food follows the crowd. Restaurants near the great monuments print menus in five languages and serve bistecca to people who have walked a very long way to eat it. None of that is fraudulent, but it is the version of Tuscan eating designed to be encountered once, by strangers, at speed.
The same hills, the same oil, the same butchers keep going well past the city walls. In the Val d'Orcia, the Casentino, the Chianti ridges and down on the Maremma coast, there are villages that hold a festival for one thing they grow or hunt, cook it for their neighbours, and put out extra tables for whoever else turns up. Fewer people go, and the ones who do tend to eat sitting down.
Of the 84 communes we have mapped in Toscana, 7 qualify as prettiest villages with a food festival: each has passed the national assessment of Italy's most beautiful villages, and each holds a recurring food festival built around one local ingredient. The smallest, Casale Marittimo, has 1,051 residents.
Elsewhere in the catalogue: The best small towns with a food festival in Toscana and The best hidden towns with a food festival that have a serious restaurant in Toscana.
Casale Marittimo
Why visit Casale Marittimo
Casale Marittimo rises on a hill at 214 meters above the Val di Cecina, fifty kilometers southeast of Pisa, the Tyrrhenian coast visible from the upper streets. The settlement here was an outpost of Etruscan Volterra in the seventh century BC; the necropolis of Casa Nocera turned up two stone statues of warrior princes, now in the Archaeological Museum of Florence, among the oldest figurative sculptures in European art.
The medieval centro is recorded as a castle of the Counts of Gherardesca by 1004, the streets arranged in concentric rings inside the old walls, stone houses pressed against the slope. Casale Marittimo carries both the Borghi più belli d'Italia and Bandiera Arancione marks, unusual for a commune of just over a thousand inhabitants.
The Chiesa di Sant'Andrea sits on the foundations of an older parish church; Palazzo Rocca and the eighteenth-century Santa Maria delle Grazie close the small loop of the centro storico.
What to see in Casale Marittimo
- Centro storico. Concentric ring of stone streets inside the medieval walls, with houses pressed against the slope and Palazzo Rocca at the top.
- Chiesa di Sant'Andrea. Parish church rebuilt on the ruins of an older pieve, the principal religious building of the borgo.
- Santa Maria delle Grazie. Eighteenth-century church on the lower edge of the centro storico, simple Tuscan late-Baroque façade.
How to get to Casale Marittimo
There is no station we could confirm here, so this one means driving. Livorno is roughly 50 minutes away by road.
Our tip
April through June brings the warm coastal hills into their best season, evenings still cool on the ridge. September and October are dry and clear, the harvest in the surrounding vineyards followed by the olive pick. July and August are hot in the Val di Cecina, but the sea breeze reaches the upper streets and tempers the worst of it. Sagra della Tagliata Mare e Terra falls in July.
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.
Greve in Chianti
Why visit Greve in Chianti
Greve sits at 236 meters in the Val di Greve, thirty-one kilometers south of Firenze and forty-two north of Siena, on the small fast river that gave the town its name. The valley narrows here enough that the road to Firenze runs past the castle estates on the slopes to the north before dropping into the town itself, and the walled hamlet above Greve looks down on the piazza from its kilometer of higher ground, a settlement some centuries older than the square below it, its tenth-century walls predating the piazza's sixteenth-century arcades.
The piazza is the point around which the rest of the town organizes itself: shops and a market under the arcades, a rebuilt church closing its south end, and the roads out toward the castles and the hamlet all beginning at its edges. The Saturday market fills the piazza.
The wine festival in early September empties the surrounding cellars into glasses for three days. What holds the place together is the geography more than any single monument: a market town at a river crossing, ringed by the vineyard slopes and the older hill settlement that all feed into the same triangular square.
What to see in Greve in Chianti
- Piazza Matteotti. The arcades shelter wine shops, butchers and pasticcerie, wrapped around the irregular triangle of paving with the navigator's bronze figure watching the center.
- Chiesa di Santa Croce. Neoclassical parish church on the south point of the piazza, rebuilt in the nineteenth century after earthquake damage.
- Castello di Verrazzano. Vineyard estate on the hills north of town, producing Chianti Classico on slopes tied to the family name that reached New York Bay.
How to get to Greve in Chianti
There is no station we could confirm here, so this one means driving. Firenze is roughly 44 minutes away by road.
✷ We have written about Greve in Chianti
“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 Greve in Chianti →Road to Siena | The Long Way Is the Better Way
Our tip
April through June and September into October are the months when the Chianti hills are at their best, green or gold depending on the harvest. July and August push past thirty degrees and the piazza empties between two and five. The wine harvest runs late September and the cellars open in turns. Expo Chianti Classico falls in September.
Piombino
Why visit Piombino
Piombino sits on a triangular promontory pointing southeast into the Tyrrhenian, at the northern edge of the Maremma. The town was founded in the ninth century by refugees from the Etruscan port after Greek pirates attacked the city; they called the new settlement Populino, small Populonia, and the name shortened over time to what it is now.
The old city, now a frazione north on the coast, became the source of the newer town's name rather than the other way round. In the medieval period Piombino became an independent signoria under the Appiani, who ruled from here over a small state that reached out to the islands across the water.
The castle at the seafront, the piazza cantilevered out over the cliff toward Elba, and the working ferry port make up the contemporary town, each looking the same direction the refugees once looked back from: toward the older settlement to the north and the channel to the islands beyond it. The Bandiera Blu coast covers the four kilometers between the port and the old acropolis, so that the walk from new town to old runs along the same shoreline that separates them by name only.
What to see in Piombino
- Castello di Piombino. Principal defensive fortress of the city on a headland pointing southeast into the sea, with the Torrione, the Rivellino and the Cittadella complex, now a museum.
- Piazza Bovio. Long rocky breakwater extending into the sea as La Rocchetta, terraced as a piazza, with a balcony view across the channel to Elba.
- Parco Archeologico di Baratti e Populonia. Chamber tombs from the seventh to second centuries BC cut into the ground of the Gulf of Baratti, laid out for walking among the excavated structures rather than viewed from a distance.
How to get to Piombino
There is a railway station in the town, so you can arrive without a car and never need one while you are here. Livorno is roughly 77 minutes away by road.
✷ We have written about Piombino
“That is the thing the young man on the beach did not see, and the man who lives here cannot stop seeing. This is an industrial coast wearing a beach towel. Run it back far enough and the whole of it, the swamp and the steel and the slag and the white water, is one long story about iron, and the holiday is the costume the story put on after the work ran out.”
Read our piece on Piombino →The Iron Coast | The Wrong Sea
Our tip
May, June, September and October are the months when the Piombino promontory is at its best, sea warm enough to swim and the ferry to Elba running every hour without the August crush. July and August are full season, with the centro storico filling by late morning and the Baratti beach turning over twice a day. November through March is cold and windy on the promontory, with limited ferry crossings and many seaside trattorie closed. Sagra del Pesce - Piombino falls in July.
Lucignano
Why visit Lucignano
Lucignano sits at 400 meters on a hill in the Valdichiana, halfway between Siena and Arezzo, built on a tight elliptical plan of four concentric rings of streets. Its position made it one of the most contested settlements of medieval Toscana: Siena, Arezzo, Florence and Perugia all fought over it between 1200 and 1500.
The current walls and three gates date to a Sienese reconstruction of 1371. In the Museo Civico inside the Palazzo Comunale stands the Albero d'Oro, a 260-centimeter Gothic gold-and-coral reliquary in the shape of a tree, begun by Ugolino di Vieri in 1350 and finished by Gabriello d'Antonio in 1471.
Local tradition turned it into the Albero dell'Amore, a marriage charm. The Collegiata di San Michele Arcangelo dominates the highest ring of the borgo, and the elliptical plan is best read from the air, which is why drone footage of Lucignano keeps appearing in articles about medieval Tuscan urbanism.
What to see in Lucignano
- Albero d'Oro. 260-cm Gothic reliquary in the shape of a tree, gold, coral and enamel, begun by Ugolino di Vieri in 1350 and completed by Gabriello d'Antonio in 1471.
- Centro storico ellittico. Four concentric rings of streets inside elliptical walls, the most complete example of medieval Tuscan elliptical town planning.
- Collegiata di San Michele Arcangelo. Eighteenth-century church on the highest ring of the borgo, with a Vasari façade adjustment and a baroque organ inside the medieval shell.
How to get to Lucignano
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 65 minutes away by road.
Our tip
April through June and September into October are the months Lucignano keeps its balance, the Valdichiana green or gold depending on the half and the centro storico cool inside its elliptical walls. The Maggiolata, a flower festival between the four quarters of the borgo, runs across the last two Sundays of May. July and August push the valley past thirty and the centro storico thins after lunch. Sagra della Filiera del Tartufo Marzuolo falls in March.
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.
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.
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