The 10 best small hill towns in the province of Siena
The province of Siena is ridge country. Towns sit where the rock allowed them, walled and compact, built of pale travertine, warm brick and the local sandstone, with streets that climb rather than wander. Autumn is the season the land shows its full range: new oil in the frantoi, pici with garlic and tomato or with a duck ragù, pecorino from Pienza's dairies, cinta senese salami, Vino Nobile and Chianti Classico poured young in bars where the football is on. In winter the clay hills of the Crete Senesi go bare and grey-brown, and the cypress lines look drawn on.
Most people come for Siena itself, and understandably, since the Campo and the Duomo and the Palio hold more per square metre than almost anywhere in Tuscany. That means coach parks, timed entries, and the long queues that build along Via di Città through the middle of the day. San Gimignano, over the border in the same tourist circuit, absorbs the overflow and its main street can feel like a corridor. Both are worth the effort, but neither is quiet, and neither is small.
The same hills continue in every direction past the city walls. The ridges that carry the famous views carry these towns too, some fortified against Siena, some built by it, all of them still small because the ground under them never permitted growth. Some sit above the Val d'Orcia with Monte Amiata filling the southern sky, others in oak woods, in Chianti vineyards, or above the Ombrone. They are the places on this list, and they reward a slow drive and a night rather than a stop.
Of the 20 communes we have mapped in the province of Siena, 17 qualify as hill towns: each is an inland hill settlement built on ground too steep to spread. This list is the small ones, 10 in all, ordered smallest first. The smallest, Radicofani, has 1,060 residents.
Elsewhere in the catalogue: The best small olive oil towns in the province of Siena and The best small hill towns with a serious restaurant in Toscana.
Trequanda
Why visit Trequanda
Trequanda is three villages in one comune: Trequanda itself at 453 meters, Castelmuzio, and Petroio at 486 meters, scattered across the hills southeast of Siena. The first written record dates to 1198, when the Cacciaconti of Scialenga held it as fief; in 1211 Emperor Otto IV gave them the right to collect tolls.
In 1553 the village was among the first to be annexed to the Grand Duchy of Tuscany. The Cacciaconti castle still anchors the centro storico, the Pieve dei Santi Pietro e Andrea next to it, built from 1327 in a Gothic-Romanesque mix and renovated in the Renaissance.
Petroio has produced fine ornamental terracotta since the early sixteenth century: lions and dogs and pineapples and chimney pots, the surface of half the gardens in central Tuscany. The municipality holds the Orange Flag from the Italian Touring Club and was inscribed in 2018 in the national register of historic rural landscapes.
What to see in Trequanda
- Castello dei Cacciaconti. Medieval fortress at the center of Trequanda, seat of the Cacciaconti di Scialenga from the twelfth century.
- Pieve dei Santi Pietro e Andrea. Gothic-Romanesque parish church begun in 1327, expanded in the Renaissance, holding a fresco attributed to Sodoma.
- Castelmuzio. Walled hilltop frazione between Trequanda and Pienza, on the rural landscape register, the smallest of the three borghi.
How to get to Trequanda
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 70 minutes away by road.
Our tip
April through June brings the green months across the Crete Senesi, the clay hills holding their color before the summer burn. September and October are dry and gold, the olive harvest running through November in the Petroio and Castelmuzio frantoi. July and August touch thirty-six degrees and the three borghi go quiet between four and seven in the afternoon.
Chiusdino
Why visit Chiusdino
Chiusdino was founded under Lombard rule between 568 and 569, on a metalliferous hill between the Val di Farma and the upper Merse. The village sits at 564 meters; five kilometers below it, on the floor of the Merse valley, the ground opens into flatter pasture where the Cistercians later built.
The two sites read as a pair: the hill town where a wealthy knight was born around 1148, and the valley floor where, a century later, an entire abbey rose to mark what he had done above it on Monte Siepi. Galgano climbed that hill on Christmas Day 1180, drove his sword into a rock as a cross, and lived as a hermit until he died the following year.
Pope Lucius III canonized him in 1185. Metallurgical analysis has dated the blade still fixed in the stone to the late twelfth century, which places the object itself in the period the story claims for it.
The Cistercians who built below, between the 1220s and 1280s, worked in the French Gothic style at the scale of a cathedral; when the roof came down in 1786 it was never replaced, and the church has stood open to the weather since. A hill settlement, a hermit's rock above it, and an unroofed church on the valley floor below: three sites at different elevations, each holding a different stage of the same account.
What to see in Chiusdino
- Abbazia di San Galgano. Built 1220s-1280s in French Gothic, the largest open-air church in Italy: a nave and side aisles standing without a roof, arches framing sky instead of vaulting.
- Cappella di Montesiepi. A round chapel raised over the stone where Galgano's sword is still lodged, the blade visible through a case set into the rock.
- Centro storico di Chiusdino. A hill village with the house where Galgano was born and the Pieve di San Michele Arcangelo standing at the highest point.
How to get to Chiusdino
There is no station we could confirm here, so this one means driving. Firenze is roughly 112 minutes away by road.
Our tip
April through June and September through October are the months the Merse valley shows best: green or gold depending on the season, the abbey light coming in at low angle through the empty windows. Concerts and theater are staged inside the roofless church in summer evenings. July and August touch thirty-five degrees; the centro storico empties between four and seven in the afternoon.
Murlo
Why visit Murlo
Murlo sits at 314 meters on a wooded ridge above the Crevole river, twenty kilometers south of Siena. The comune is scattered.
The town hall is in Vescovado, the modern center down on the valley road; the medieval castle of Murlo, walled and tower-anchored, is a kilometer up on the hill, mostly empty and given over to tourism. The bishops of Siena held this ground as a feudal lordship for centuries, which kept it outside the Sienese republic and gave it the unusual status of an episcopal fief.
The defining find is older. On Poggio Civitate, three kilometers north, archaeologists from 1966 onward uncovered an Etruscan princely palace of the seventh and sixth centuries BC, one of the most important Etruscan settlement complexes ever excavated.
The terracotta acroteria from the roof line included the Cappellone, a seated bearded male wearing a wide-brimmed hat, sixth century BC, now the symbol of the Antiquarium museum housed in the old Episcopal Palace at the center of the borgo.
What to see in Murlo
- Antiquarium di Poggio Civitate. Archaeological museum in the medieval Palazzo Vescovile at the center of Murlo, holding the Cappellone and other finds from the Etruscan settlement on Poggio Civitate.
- Poggio Civitate. Etruscan princely palace complex of the seventh and sixth centuries BC, three kilometers north of the borgo, one of the most important sites in Etruria.
- Castello di Murlo. Twelfth-century walled village, the medieval seat of the bishops of Siena, with narrow streets converging on the Palazzo Vescovile.
How to get to Murlo
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 104 minutes away by road.
Our tip
April through June and September into October are the months when the Crete Senesi south of Murlo sit at their gold-and-green best. The Antiquarium is open year-round but limited in winter hours. July and August push past thirty-three degrees and the castle empties between two and six.
Radicofani
Why visit Radicofani
Radicofani sits where the rolling clay hills of the Val d'Orcia give way, abruptly, to a volcanic cone: the town rises straight off the plain rather than sitting among gentler slopes, which is why the rock is visible from Pienza, Montalcino, the Cassia road and points as far off as Lago Trasimeno, 60 km away, and why it reads as a landmark rather than a village from any distance. The medieval centro climbs in the same volcanic-basalt stone as the rock beneath it, narrowing as it rises, so that the streets themselves seem to funnel a visitor upward toward the fortress that caps the summit.
That fortress began under the Aldobrandeschi in the 12th century, was expanded by the outlaw and Ghibelline noble who made the rock his raiding base from 1297 to 1303, robbing pilgrims and churchmen on the road below and returning the richest captives to Pope Boniface VIII with gallows-humour notes attached, a story Dante folds into Purgatorio VI and Boccaccio into the Decameron's tenth day. The Sienese extended it again in the 14th century, the Medici in the 16th after Cosimo I bought the territory in 1556, and a powder-magazine explosion in 1735 took off the upper levels, leaving the restored lower fortress and its terrace standing today.
Below the village, at its foot rather than within its walls, sits the old stagecoach inn, a separate register of the town's history: not the fortress and its outlaw but the machinery of travel and hospitality that grew up beneath it to serve the pilgrim road running from Canterbury to Rome, hosting Montaigne, Dickens and Grand Tour travellers moving between Florence and Rome from 1500 to 1850. The town's church, the Romanesque Pieve di San Pietro, and its companion the Chiesa di Sant'Agata, with its Della Robbia altarpiece, belong to the centro itself rather than to the rock above it.
Surroundings widen the picture: Pienza, also UNESCO-listed, lies 30 km north, Montalcino 35 km northwest, and the extinct volcano immediately west offers a cooler, wooded counterpoint of chestnut and beech forest to the bare rock the town is built on, with thermal baths built around a pool 20 km north. The food follows the same Val d'Orcia line as its neighbors: pici with hare ragù, pecorino di Pienza, lardo di Colonnata and finocchiona, with Brunello di Montalcino and Vino Nobile di Montepulciano within easy reach.
The Festa Medievale in mid-July recreates the outlaw court that once ruled the summit, and the Festa del Fagiolo in early August celebrates the local cannellini bean. Like other Val d'Orcia hilltop villages, the population has fallen hard, from 2,800 in 1951 to 1,060 today.
The three marks the town carries together, UNESCO, Bandiera Arancione and the pilgrim route, are not separate honors so much as three ways of naming the same fact: a place built for defense and passage that has outlasted both purposes and now stands mostly for itself.
What to see in Radicofani
- Rocca di Radicofani. 12th-c Aldobrandeschi origin, expanded by the Sienese in the 14th century and by the Medici in the 16th, after Cosimo I bought the territory in 1556. A 1735 powder-magazine explosion destroyed the upper levels. The restored lower fortress and its panoramic terrace give the most expansive single view in southern Tuscany.
- Via Francigena + Posta Medicea. The inn stands at the foot of the village, on the pilgrim road from Canterbury to Rome, where it once put up travellers moving between Florence and Rome for three and a half centuries, among them Montaigne and Dickens.
- UNESCO Val d'Orcia centro. An intact medieval centro climbing in volcanic-basalt stone toward the fortress above it. The Pieve di San Pietro is Romanesque; the Chiesa di Sant'Agata holds a Della Robbia altarpiece.
How to get to Radicofani
There is no station we could confirm here, so this one means driving. Perugia is roughly 91 minutes away by road.
✷ We have written about Radicofani
“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 Radicofani →Val d'Orcia | The Postcard Is Constructed
Our tip
Radicofani is best May–September. The Festa Medievale mid-July (Ghino di Tacco pageant) + Festa del Fagiolo early August are the year's headline events. Summer is hot in the Val d'Orcia but the 814m altitude keeps Radicofani 5-7°C cooler than the lower valleys. Festa degli antichi mestieri a Radicofani falls in June.
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.
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.
Castiglione d'Orcia
Why visit Castiglione d'Orcia
The village stands on a ridge where the land drops toward the Val d'Orcia, the agricultural landscape shaped by Sienese painters and Renaissance estate managers that stretches between Siena and the mountain to the south. First documented in 714, the settlement was then held by the Aldobrandeschi, who built the fortress above the village to hold the medieval road running between the mountain and the Via Francigena, the pilgrim route below.
Siena took the town in 1251 and passed control to the Salimbeni and later the Piccolomini, a shift that put a Sienese family in charge of the second fortress on the neighboring outcrop in the frazione of Rocca d'Orcia. The village center and its outlying frazione form two working parts of one settlement: the walled hill town with its civic square and parish church, and the fortified outcrop a short distance off that once policed the valley approach on its own.
The territory is one of three communes sharing the UNESCO inscription, a status that recognizes the whole valley rather than any single settlement within it. What the record shows, across all of it, is a place whose function was always defensive and administrative before it was scenic: two fortresses set to watch one road, a town divided between them, and a landscape that outgrew its original purpose to become the reason people look at it now.
What to see in Castiglione d'Orcia
- Rocca Aldobrandesca. Aldobrandeschi fortress above the village, documented from the eighth century, walls and keep open as an archaeological site.
- Rocca a Tentennano. Stronghold on a basalt outcrop in the frazione of Rocca d'Orcia, reached by a climb that still shows the defensive logic of the site, controlling the approach along the valley.
- Piazza Vecchietta. Small triangular civic square in the centro storico, the space that carries the painter's adopted name through the village center he left behind.
How to get to Castiglione d'Orcia
There is no station we could confirm here, so this one means driving. Perugia is roughly 152 minutes away by road.
Our tip
April through June and September into October are the months the Val d'Orcia photographers come for, the green hills and the gold stubble depending on the half. The borgo at 540 meters stays cool when the valley floor heats up. July and August push the lower fields into the mid thirties; afternoons thin out the centro storico but the ridge keeps a breeze.
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.
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.
Castellina in Chianti
Why visit Castellina in Chianti
Castellina in Chianti sits at 578 meters on the watershed between the Arno and Ombrone basins, fifteen kilometers northwest of Siena and thirty-five south of Florence. Its position on the historic frontier between the two republics shaped the town: it was a Sienese border fortification reinforced in the fifteenth century by Filippo Brunelleschi and Giuliano da Sangallo against firearm warfare.
The Rocca with its fifteenth-century tower dominates the centro storico and now houses the Museo Archeologico del Chianti Senese, opened in 2006. The Via delle Volte runs the length of the eastern wall: an original ancient pomerium, once open to the sky, gradually built over by private houses against the wall and now a covered arcaded passage lined with workshops and trattorie.
The Tumulo Etrusco di Montecalvario, a sixth-century BC tomb with four burial chambers carved on the cardinal axes, sits a kilometer from the centro storico. The Gallo Nero of Chianti Classico DOCG is grown on the slopes below.
What to see in Castellina in Chianti
- Rocca di Castellina. Fifteenth-century fortification with imposing keep, now housing the Museo Archeologico del Chianti Senese, opened in 2006.
- Via delle Volte. Covered arcaded walkway along the eastern wall, once an open pomerium, built over by houses pressing against the fortifications and now lined with workshops.
- Tumulo di Montecalvario. Sixth-century BC Etruscan tomb a kilometer from town, with four burial chambers carved on the cardinal compass points, excavated in the early 1900s.
How to get to Castellina in Chianti
There is no station we could confirm here, so this one means driving. Firenze is roughly 63 minutes away by road.
✷ We have written about Castellina 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 Castellina in Chianti →Road to Siena | The Long Way Is the Better Way
Our tip
April through June and September into October are the working months on the Chianti watershed: vine work, harvest from mid-September, mild days at 578 meters. The Festa del Vino in the second half of September fills the centro storico for a long weekend. July and August are warmer but stay below the inland Maremma heat, and the Via delle Volte is reliably cool.
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.
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.
Buonconvento
Why visit Buonconvento
Buonconvento sits on the plain of the Via Cassia at 147 meters, where the Arbia meets the Ombrone, twenty-five kilometers south of Siena and the main town of the Crete Senesi. The name comes from bonus conventus, happy meeting place, recorded for the first time in 1100.
In August 1313 Emperor Henry VII of Luxembourg died here on his way to Rome, a death the Ghibellines blamed on poisoning. The Sienese walled the borgo in 1379: brick curtain walls with hanging arches, two gates called Porta Senese and Porta Romana.
Porta Romana was destroyed in 1944 by the retreating Germans, the same year the Allies came up the Via Cassia. The Palazzo Pretorio, fourteenth century, has twenty-five podestà coats of arms on its façade and a tower that echoes Siena's Torre del Mangia.
The Museo d'Arte Sacra della Val d'Arbia holds a Madonna by Duccio di Buoninsegna from the 1290s.
What to see in Buonconvento
- Palazzo Pretorio. Fourteenth-century brick palace with twenty-five podestà coats of arms on its façade and a slender tower modeled on Siena's Torre del Mangia.
- Mura di Buonconvento. Brick curtain walls with hanging arches built by Siena in 1379, with Porta Senese to the north (Porta Romana lost in 1944).
- Museo d'Arte Sacra della Val d'Arbia. Sacred art collection in Palazzo Ricci Socini covering the Sienese school from the 13th to 19th centuries, including a Duccio Madonna.
How to get to Buonconvento
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 99 minutes away by road.
Our tip
April through June paints the Crete green and the spring wheat is at full height by May. September and October are the Crete at their most photographed: bare hills back in clay color, low sun, long shadows. July and August touch the high thirties in the plain; the walls hold heat into the night.
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