The prettiest villages with a medieval festival in Toscana
Tuscany builds in sandstone, tufo and pale plaster, and the villages that sit above its vineyards and chestnut woods keep their shape because nobody ever had reason to change it. In summer the festival season arrives with drums, crossbows, borrowed armour and long trestle tables set out under the walls, and the food is whatever the surrounding land grows: bread without salt, wild boar cooked slowly, pecorino, hand-rolled pici, chestnut flour in the mountains and tomatoes on the Maremma plain. Spring and early autumn are the better months for walking between them, when the light is low and the hill roads are empty. The archways and towers are the same ones the processions were designed around.
People come to Tuscany for the Palio in Siena, and they are right to want to see it, but the Campo fills to capacity long before the horses run and accommodation in the city is booked out for months either side. The result is one afternoon of spectacle experienced through a crowd, at a price set by demand. Most visitors then go back to Florence and never see a festival anywhere else in the region.
The same tradition runs the length of Tuscany, through the Garfagnana, the Val d'Orcia, the Maremma and the hills of the Valtiberina, in villages small enough that the whole population takes part. Fewer people go to these, which means you can stand at the front, eat at the communal supper, and speak to the people in costume afterwards. The towns here have each been assessed as among Italy's most beautiful villages, and each stages a historical re-enactment that recurs year after year.
Of the 84 communes we have mapped in Toscana, 8 qualify as prettiest villages with a medieval festival: each has passed the national assessment of Italy's most beautiful villages, and each stages a recurring historical re-enactment. The smallest, San Casciano dei Bagni, has 1,500 residents.
Elsewhere in the catalogue: The prettiest hidden villages with a serious restaurant in Toscana and The best small towns with a medieval festival in Toscana.
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
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.
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
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.
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.
The re-enactment here is Memorie dal passato a Lucignano, usually held in September.
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.
Why visit Castiglione di Garfagnana
Castiglione di Garfagnana sits at 540 meters on the road to the San Pellegrino pass, in the upper Serchio valley, surrounded by chestnut woods and the Apuan and Apennine ridges. The Romans built a castrum here, the Castrum Leonis, to command the route between Lucca and Modena; what stands now is the thirteenth-century walled town, with three Torrioni and a Rocca that still anchor the south flank.
Through the fifteenth and sixteenth centuries, while the rest of the Garfagnana fell to the Este of Ferrara and was administered by Ariosto from nearby Castelnuovo, Castiglione held for the Republic of Lucca. The Estensi besieged it in 1603 and 1613 without taking it.
The Pieve di San Pietro Apostolo, the oldest church in the borgo, was first built in 723 by two Lombard brothers and rebuilt in the twelfth century. In winter the trattorie serve chestnut polenta with boiled pork bones, the standard cold-weather dish of the valley.
The re-enactment here is Festa Medievale di Castiglione di Garfagnana, usually held in August.
What to see in Castiglione di Garfagnana
- Rocca medievale. Thirteenth-century fortress with three Torrioni, the symbol of Castiglione and the anchor of the medieval walls.
- Mura medievali. Well-preserved thirteenth-century walls with large defensive towers ringing the borgo, intact for most of their length.
- Pieve di San Pietro Apostolo. Oldest church in town, first built in 723 by two Lombard brothers and rebuilt in the twelfth century by Bishop Guido III of Lucca.
How to get to Castiglione di Garfagnana
Pisa is roughly 95 minutes away by road.
✷ We have written about Castiglione di Garfagnana
“There are two ways to drive from Aulla to Lucca. The first is the one everyone takes: the coast, the A12, the cruise control, ninety minutes of the same Tyrrhenian to your right. The second is the one we took with Daniel, on a clear day in November, and it is two and a half hours longer if you stop, but it is in a different country.”
Read our piece on Castiglione di Garfagnana →Apuan Roadtrip | A Steak, a Friend, and the Long Way Down to Lucca
Our tip
May through September is the high season in the Garfagnana, the chestnut woods and the Apennine passes open and warm in the day, cool at night. June and July bring the long evening light at 540 meters; August is busy but never coastal-hot. October is the chestnut harvest, the dish of polenta di castagne starts to appear on menus, the Sagra della Castagna runs the third weekend. Festa Medievale di Castiglione di Garfagnana falls in August.
Why visit Suvereto
Suvereto sits at 127 meters on the inland edge of the Val di Cornia, twelve kilometers from the Tyrrhenian coast. The name comes from the Latin suberetum, a wood of cork oaks, and the surrounding forests still hold them.
The Rocca Aldobrandesca, first documented in 973, occupies the highest point of the borgo; the Aldobrandeschi family who controlled it also ruled large sections of southern Toscana and the Maremma. The town reached its golden age in the thirteenth century, when Frederick II granted it a charter of freedoms in 1216 and the Palazzo Comunale was built.
The centro storico is a tight grid of stone vicoli that runs uphill from the Romanesque Pieve di San Giusto to the fortress. Suvereto carries five institutional signals at once, a rare combination in the province of Livorno, and the surrounding wine country falls under the Val di Cornia DOC and Suvereto DOCG appellations.
The re-enactment here is Palio dell'Imperatore, usually held in August.
What to see in Suvereto
- Rocca Aldobrandesca. Fortress at the highest point of the borgo, documented from 973, expanded in the twelfth century and partly restored as an open archaeological site.
- Pieve di San Giusto. Eleventh-century Romanesque parish church at the foot of the borgo, with a sandstone façade and a single nave divided by stone columns.
- Palazzo Comunale. Thirteenth-century town hall with a double external staircase and Ghibelline merlons, one of the earliest surviving civic palaces of the Maremma.
How to get to Suvereto
Livorno is roughly 84 minutes away by road.
✷ We have written about Suvereto
“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 Suvereto →The Iron Coast | The Wrong Sea
Our tip
April through June and September into October are the dry months in the Val di Cornia, when the cork forests behind the town hold their light and the wine harvest runs in September. The Sagra del Cinghiale, celebrating the wild boar of the surrounding hills, runs across two weekends in December and draws a different crowd. July and August are hot at 127 meters and most visitors descend to the Tyrrhenian coast in the afternoon. Palio dell'Imperatore falls in August.
Why visit Manciano
Manciano sits at 444 meters on a hill in the southern Maremma grossetana, with a 360-degree view that runs from Monte Amiata north to the Tyrrhenian coast. The Aldobrandeschi held the original stronghold from the twelfth century.
Siena occupied the town between 1419 and 1455 and built the Rocca that still dominates the centro storico, a square keep with battlements on a shoe-base. After 1455 it returned to local rule and passed eventually to the Medici Grand Duchy.
The comune is large by Toscana standards and includes some of the best-known places of the southern Maremma: Saturnia, the Etruscan town built around its sulphurous hot springs, and Montemerano, a small walled borgo on the road to the Lago di Bolsena. The Albegna and Fiora valleys, which the town once served as a regional market, still meet at its foot.
Wine, olive oil and wild boar work the territory in roughly the order they sit on a Maremmano menu.
The re-enactment here is Palio delle Botti di Manciano, usually held in August.
What to see in Manciano
- Rocca Aldobrandesca. Sienese fortress of 1424 on Aldobrandeschi foundations, square keep, walls with battlements and a solid shoe-base, dominating the centro storico.
- Saturnia. Etruscan town and frazione south of Manciano, with medieval walls, remains of a Roman road and the sulphurous hot springs used since antiquity.
- Montemerano. Small walled borgo east of Manciano, three concentric circles of streets and a fifteenth-century Madonna della Gattaiola in the parish church.
How to get to Manciano
Terni is roughly 132 minutes away by road.
✷ We have written about Manciano
“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 Manciano →Maremma | The Last Cowboys of Tuscany
Our tip
April through June and September into October are the months Manciano shows the southern Maremma at its best, the territory dry but green, the Saturnia pools warm against cool mornings. The Sagra dell'Anatra runs in mid-August. July and August are hot at 444 meters but easier than the coast; afternoons in the centro storico empty between two and six. Palio delle Botti di Manciano falls in August.
Why visit Monte Argentario
Monte Argentario is a peninsula on the southern Tuscan coast, 35 kilometers south of Grosseto, connected to the mainland by three sand spits that enclose the lagoons of Orbetello. The mountain at its center rises to 635 meters, and the two seats of the comune sit at sea level on opposite sides of it, the northern harbor facing toward Grosseto, the southern one turned toward the open coast below.
The history of the peninsula splits from the rest of Tuscany after 1557, when the territory was carved out of Sienese land and handed to the Spanish crown, which spent the next century and a half fortifying the coastline against corsair raids rather than building the kind of inland towns found elsewhere in the region. The result is a place organized around its edges rather than a center: two ports facing different waters, a mountain of forts between them, and a coastal road that ties the whole shape together for anyone crossing from one harbor to the other.
What the peninsula adds up to is a piece of Tuscany that spent its formative centuries as a Spanish military frontier, and still wears that history in its two-harbor shape and the ring of stone above them.
The re-enactment here is Palio Marinaro dell'Argentario, usually held in August.
What to see in Monte Argentario
- Forte Stella. Six-pointed star fort above Porto Ercole, designed for the Spanish by Buontalenti and Camerini and completed in the mid-1600s as part of the Presidi defense system.
- Forte Filippo. Spanish bastioned fortress above Porto Ercole, named for Philip II and built in the late 16th century to protect the Stato dei Presidi from corsair raids.
- Rocca Aldobrandesca, Porto Ercole. Earlier Aldobrandeschi fortress incorporated into the Spanish defense system, dominating the harbor and the old town of Porto Ercole.
How to get to Monte Argentario
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 137 minutes away by road.
Our tip
May through September is the season on the peninsula. Porto Santo Stefano and Porto Ercole fill in July and August; the Palio Marinaro on August 15 doubles the population of Porto Santo Stefano for a single afternoon. June and September are the easiest months, with warm water and fewer day-trippers. Palio Marinaro dell'Argentario falls in August.
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
Perugia is roughly 82 minutes away by road.
Our tip
April through June and September into October are the working months in the Valtiberina: dry days, low cloud over the upper Tiber, the surrounding farmland green or gold by season. The Mostra Mercato dell'Artigianato runs the last week of April and the first week of May, filling the streets with artisans from across the valley. Late June marks the anniversary of the 1440 battle, with reenactments below the walls. Palio della Vittoria di Anghiari falls in June.
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