The 9 best hidden hill towns on a walking route in Toscana
Walking is the honest way to read this landscape. The old routes climb out of one river valley and drop into the next, past oak scrub and ploughed clay, and every few hours a town appears on a ridge, built from the stone underneath it: travertine in the south, brick and tufo further north, dark sandstone in the Lunigiana. Late spring and early autumn are the seasons for it, when the crete are green or freshly turned and the heat has gone out of the middle of the day. At the end of a stage there is pecorino di Pienza, pici with garlic, a glass of Brunello or a bowl of testaroli, and a bed inside walls that were built to shelter people arriving on foot.
Most visitors take the Toscana that fits in a car and a week. Siena absorbs the crowds, its Campo full from morning until the light goes, and the coach parks below the walls fill again the next day with people who will see the cathedral, eat near the piazza and leave. It is a great city and it deserves the attention. It also means the countryside beyond it is understood as scenery viewed through a windscreen rather than ground to be crossed.
The same hills carry on past the city, and the walking routes carry on with them, over the Apennine passes, down the Elsa valley, through the Val d'Orcia and up to the volcanic cone in the south. The towns along those stages are the ones in this list. Fewer people arrive at them, and most who do arrive with a pack and mud on their boots.
Of the 84 communes we have mapped in Toscana, 13 qualify as hill towns on a walking route: each is an inland hill settlement, and each is a stage on one of the long historic walking routes. This list is the hidden ones, 9 in all, ordered smallest first. The smallest, Radicofani, has 1,060 residents.
If you are still choosing, we have also written The best towns on a walking route in the province of Siena and The best hidden towns with a medieval festival in the province of Siena.
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.
Pontremoli
Why visit Pontremoli
Pontremoli sits at 236 meters where the Magra and the Verde meet, the northern gate of Tuscany and the historic capital of Lunigiana. The Via Francigena crossed here on the descent from the Cisa pass, which is why the town's medieval bridges, the Ponte della Cresa and the Ponte del Casotto, still carry pilgrim traffic eight centuries later.
The Castello del Piagnaro above the centro storico holds the Museo delle Statue Stele Lunigianesi: anthropomorphic sandstone figures carved between 3000 and 200 BC, eighty of them recovered from the surrounding hills, unique to this corner of Italy. The Bancarella Prize, awarded by the town's traveling booksellers since 1953, made Pontremoli the only Italian commune where a literary prize was founded by the people who actually sell books rather than write them.
The local plate is testaroli, a Ligurian-Lunigiana flatbread cut into diamonds and eaten with pesto or olive oil.
What to see in Pontremoli
- Castello del Piagnaro. Tenth-century fortress on the hill above town, named for the slate roof tiles (piagne), housing the Museo delle Statue Stele.
- Museo delle Statue Stele Lunigianesi. Eighty anthropomorphic stone figures carved between 3000 and 200 BC, the densest concentration of Copper Age stele in Europe.
- Concattedrale di Santa Maria Assunta. Seventeenth-century baroque cathedral with a single nave and a domed presbytery, on Piazza del Duomo.
How to get to Pontremoli
There is a railway station in the town, so you can arrive without a car and never need one while you are here. Parma is roughly 81 minutes away by road.
Our tip
April through June brings the rivers full and the chestnut woods green. The Premio Bancarella runs in late July on Piazza della Repubblica, the busiest week of the year. August is hot but cooler than the coast, with festivals across the Lunigiana valley. Medievalis a Pontremoli falls in August.
Cerreto Guidi
Why visit Cerreto Guidi
Cerreto Guidi sits at 123 meters above the Padule di Fucecchio, thirty kilometers west of Florence, on the old hunting grounds of the Counts Guidi and later the Medici. Cosimo I commissioned the Villa Medicea here between 1564 and 1567 as a hunting lodge and territorial outpost over the marsh.
The villa is mounted on a scenographic base of four symmetrical ramps of stairs, the ponti medicei, traditionally attributed to Bernardo Buontalenti, designed to raise the perspective plane and the level of the entrance. In 2013 the villa entered the UNESCO list of Medici Villas and Gardens of Tuscany along with twelve others, and it remains one of the few permanently open as a museum, housing the Museo Storico della Caccia e del Territorio since 2002.
The Via Francigena passes a few kilometers south. Isabella de' Medici, daughter of Cosimo I, was strangled in this villa by her husband Paolo Giordano Orsini in July 1576.
What to see in Cerreto Guidi
- Villa Medicea di Cerreto Guidi. Hunting villa built for Cosimo I de' Medici between 1564 and 1567, UNESCO World Heritage since 2013, holding the Museo Storico della Caccia.
- Ponti Medicei. Four symmetric ramps of stairs attributed to Buontalenti, supporting the villa above the village and forming its scenographic base.
- Museo Storico della Caccia e del Territorio. Hunting and local history museum housed in the villa since 2002, with weapons, prints and documents from the Medici hunting grounds.
How to get to Cerreto Guidi
There is no station we could confirm here, so this one means driving. Firenze is roughly 50 minutes away by road.
Our tip
April through June is the easiest time to walk the village and the villa garden, with the Padule di Fucecchio at its greenest. September and October dry the marsh, the harvest in the surrounding Chianti Montalbano vineyards runs through late September. July and August are hot in the lower Arno plain and the villa is the cool place to be; visitor numbers peak around mid-August. Palio del Cerro falls in September.
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.
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.
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.
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.
San Gimignano
Why visit San Gimignano
San Gimignano sits at 334 meters in the Val d'Elsa, halfway between Firenze and Siena on the medieval pilgrim road to Rome. Patrician families built 72 tower-houses in the twelfth and thirteenth centuries as proofs of wealth and platforms for vendettas; 14 still stand, the tallest being the Torre Grossa at 54 meters.
The town declared independence from the bishops of Volterra in 1199 and grew rich on saffron and Vernaccia, the white wine grown on the surrounding hills and praised since Dante. The Black Death of 1348 broke the boom; San Gimignano lost more than half its population and submitted to Florence.
That collapse is the reason the medieval skyline survived. UNESCO listed the historic centre in 1990 as a complete record of feudal architecture.
Roughly three million visitors come each year, more than 400 times the resident population, and the centro storico empties into the surrounding olive groves once the day-trippers leave.
What to see in San Gimignano
- Torre Grossa. Fifty-four meter civic tower attached to the Palazzo Comunale, the tallest of the surviving 14, open for the climb to the panoramic terrace.
- Piazza della Cisterna. Triangular medieval square paved in brick around an octagonal well of 1287, lined by tower houses and Romanesque palaces.
- Collegiata di Santa Maria Assunta. Romanesque parish church on Piazza Duomo, walls covered by Bartolo di Fredi and Lippo Memmi frescoes of Old and New Testament scenes.
How to get to San Gimignano
There is no station we could confirm here, so this one means driving. Firenze is roughly 61 minutes away by road.
✷ We have written about San Gimignano
“We arrived in the afternoon, into the second half of the day’s crowd. Off-season meant it was groups and guides rather than a flood, but the shops were open and doing their worst, the same garbage souvenirs, the same pasta no one local would eat, and we walked through it the way you walk through a thing you have decided not to let ruin your evening. The towers stood over all of it, indifferent, which is their whole talent.”
Read our piece on San Gimignano →San Gimignano | The Town After Seven
Our tip
April through June and September into October are the months the town is worth a full day rather than three hours. The buses still come, but late afternoon empties the piazzas and lets the towers take their light. July and August push temperatures past thirty and the centro storico becomes uncomfortable between two and six, when the stone radiates heat. Fiere delle Messi di San Gimignano falls in June.
Monteriggioni
Why visit Monteriggioni
Monteriggioni sits at 274 meters on a natural hillock between Firenze and Siena, eleven kilometers from the Sienese gates. The walls were built between 1213 and 1219, when Siena ran them up as a frontline garrison facing Florentine expansion north.
They are still there. Fourteen square towers, 570 meters of curtain wall, ten meters tall, two gates: Porta Fiorentina to the north, Porta Romana to the south.
Dante used the towers in Inferno XXXI as the image for the giants ringing the central pit of Hell. The fortress was never breached by storm.
Inside, the village is a single irregular Piazza Roma, a Romanesque parish church of Santa Maria Assunta, a few streets that take fifteen minutes to walk end to end. The Via Francigena runs past the southern wall.
The town hosts a medieval festival in early July, when the population inside the walls multiplies for a weekend. The rest of the year, the silence inside the gates is the point.
What to see in Monteriggioni
- Mura di Monteriggioni. Circular 570-meter wall built 1213-1219 by the Sienese, fourteen square towers on equidistant bases, ten meters high, intact.
- Piazza Roma. Single main square inside the walls, ringed by stone houses, with the Romanesque parish church on the north side.
- Chiesa di Santa Maria Assunta. Romanesque parish church on Piazza Roma, plain stone façade, single nave, the only significant religious building inside the walls.
How to get to Monteriggioni
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 96 minutes away by road.
✷ We have written about Monteriggioni
“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 Monteriggioni →Road to Siena | The Long Way Is the Better Way
Our tip
April through June and September into October are the months when the walls and the Chianti ridge behind them sit at their best, before the heat closes in. The Festa Medievale takes the second weekend in July, three days of costumed reenactment and feasting inside Piazza Roma, when the village population multiplies. July and August are hot and the day-tripper buses from Firenze and Siena fill the gates between ten and four. Monteriggioni di torri si colora falls in July.
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