The Val d'Orcia is the farmed valley of the river Orcia south of Siena, and the hills, cypress rows and lone farmhouses of a thousand calendar photos are mostly here. Its landscape was shaped on purpose by Sienese landowners in the 14th and 15th centuries, and UNESCO listed the whole valley in 2004. The Italy page covers Brunello tasting in Montalcino, on its western edge; this page is the rest of the valley.
The towns sit on the hilltops: San Quirico d'Orcia in the middle, Pienza on its ridge to the east, Montalcino to the west and Castiglione d'Orcia to the south, with Montepulciano just over the eastern rim. Below them are hot springs that have been used since Roman times, at Bagno Vignoni and Bagni San Filippo. There is no railway with useful service and few buses, so plan on a car or a tour.
Walk Pius II's ideal town of Pienza and taste its pecorino
Pienza
Half a dayNo booking needed
A village rebuilt in about four years as a model Renaissance town, with loggias over the Val d'Orcia.
What it is
Pienza was the village of Corsignano until one of its sons, Enea Silvio Piccolomini, was elected Pope Pius II in 1458 and had the architect Bernardo Rossellino rebuild it from about 1459 as a model Renaissance town, in about four years. The result is the trapezoid Piazza Pio II, with the cathedral, the town hall and Palazzo Piccolomini, whose loggias overlook a walled Renaissance garden and the Val d'Orcia beyond. UNESCO listed the centre in 1996.
How to do it
Then walk the lanes with names like Via dell'Amore and Via del Bacio.
Good to know
Pienza is also considered the capital of pecorino, thanks to the sheep pastures of the valley, and the town celebrates the cheese on the first Sunday of September.
Time needed
Half a day
Best time
Any day; the first Sunday of September for the cheese festival
See Bagno Vignoni's square of hot water, then the mill pools
Bagno Vignoni
1 to 2 hoursFree
A village square that is a pool of thermal water, steaming on cold mornings, and warm streams spilling over a travertine cliff.
What it is
In Bagno Vignoni the village square is a pool: a long stone tank of thermal water, fed by a spring that comes out of the ground at around 50 °C, with the houses and an arcade built round it and the steam rising on cold mornings. Bathing in it is forbidden.
How to do it
Walk instead to the edge of the village and down the path into the Parco dei Mulini, where the water runs along channels and spills over a white travertine cliff past old mills cut into the rock; people sit on the edge with their feet in the warm streams. The village lies just off the Via Cassia, south of San Quirico.
Good to know
For a proper soak, the spa hotels in the village, among them the Posta Marcucci, open their outdoor thermal pools to non-guests.
Walk the Fosso Bianco to the Balena Bianca at Bagni San Filippo
Bagni San Filippo
2 hoursFree
Hot water at about 48 °C runs down a wooded stream, building white terraces, free pools and a formation called the white whale.
What it is
On the slopes of Monte Amiata, at the southern end of the valley, hot water at about 48 °C runs down a wooded stream, the Fosso Bianco, and over the centuries its minerals have built white terraces and pools. The biggest formation is the Balena Bianca, the white whale.
How to do it
A path from the village leads down through the woods, and the pools along the stream are free to use.
Good to know
The rules matter here: the Balena Bianca is a fragile formation, so you may not touch it, walk on it or bathe next to it. Come early, bring no soap, and take your rubbish away.
Find the Vitaleta chapel and the San Quirico cypresses
Between San Quirico d'Orcia and Pienza
2 hours for both stopsFree
A small white chapel framed by cypress rows and a ring of cypresses on a bare hill, a few minutes apart.
What it is
Two of the valley's most photographed sights are a few minutes apart. The chapel of the Madonna di Vitaleta was redesigned in the 19th century, and its Della Robbia Virgin now hangs in a church in San Quirico.
How to do it
The chapel, a small white church with a bell tower framed by cypress rows, stands on private land off the road between San Quirico and Pienza: follow the sign onto a short gravel road, park, and walk about a kilometre. Walkers from Pienza can take the back road from the parish church of Corsignano. Then drive to the Cipressini di San Quirico, a ring of cypresses on a bare hill beside the Via Cassia, around kilometre 189.
Good to know
Park on the verge on the San Quirico side so you do not cross the road on foot, and keep out of the fields.
A pale stone Romanesque church alone among olive groves, where alabaster capitals glow when the low sun comes in.
What it is
Sant'Antimo stands alone in a valley of olive groves about 10 kilometres south of Montalcino, below the village of Castelnuovo dell'Abate: a pale stone Romanesque church begun in the early 12th century, on the site of an abbey tradition links to Charlemagne. Inside, the alabaster capitals glow when the low sun comes through the windows.
How to do it
Combine the visit with a Brunello tasting in Montalcino.
Good to know
It is still a place of prayer, run by a religious community, and the timetable follows the liturgy: from April to September it opens 10:00 to 18:30, in October to 18:00, and from November to March 10:30 to 17:00, opening only at 11:00 on Sundays and holidays, after Mass. Vespers are at 17:30. Keep quiet during services.
Go down into Montepulciano's cellars for Vino Nobile
Montepulciano
Half a dayBook ahead
Under Renaissance palaces the rock is cut into cellars, one a vaulted hall of oak barrels its owners compare to a cathedral.
What it is
Montepulciano stands on the ridge between the Val d'Orcia and the Val di Chiana, and under its Renaissance palaces the rock is cut into cellars where its wine ages. Vino Nobile di Montepulciano, a DOCG since 1980, is made mainly from Sangiovese, called Prugnolo Gentile here, at least 70 per cent, and aged for at least two years. Two historic cellars sit in the old town: De' Ricci, on Via Ricci, where a stone staircase leads down to a vaulted hall of oak barrels its owners compare to a cathedral, and Contucci, on Piazza Grande, with cellars on three floors under a 16th-century palazzo.
How to do it
Book a visit with tasting directly with the cellar. Park below the town and walk up the Corso.
Good to know
In August the town's districts race barrels uphill in the Bravìo delle Botti.
See the village play of the Teatro Povero in Monticchiello
Monticchiello
An eveningBook ahead
Every summer since the 1960s the people of a walled hamlet have played their own lives in their own square.
What it is
Every summer since the 1960s the people of Monticchiello, a walled hamlet a few kilometres from Pienza, have written and performed a play about their own lives, the autodramma, in their own square. The 2026 edition was the 60th: L'occhio oltre, the story of a man born in June 1944 into a sharecropping family, running nightly at 21:30 in Piazza della Commenda from 25 July to 14 August, with two Mondays off.
How to do it
The pattern is the same each year, late July to mid August, and the 2027 dates are announced on teatropovero.it, where you book; there is also a phone line.
Good to know
Arrive early to eat in the village before the show, and bring a layer, since nights on the hill cool down. The play is in Italian, but the setting does much of the work.
Climb to the Rocca di Tentennano for the view down the valley
Rocca d'Orcia, Castiglione d'Orcia
1 to 2 hoursNo booking needed
A fortress on a crag with one of the widest views of the valley, from Monte Amiata to the hill towns.
What it is
The Rocca di Tentennano is the fortress on a crag above the tiny village of Rocca d'Orcia, built in the 11th and 12th centuries to watch the road through the valley, taken by Siena in 1251 and held from 1274 by the powerful Salimbeni family. Catherine of Siena stayed here and began her Dialogue within its walls. The state took it over in 1971 and restored it, and today a path leads up through the keep to a terrace with one of the widest views of the Val d'Orcia, from Monte Amiata to the hill towns.
How to do it
Walk up from the lower village of Rocca d'Orcia, past its old cistern square, and continue to Castiglione d'Orcia, just across the hill.
Good to know
It is part of the Siena museums network, with a small entry fee.
Taste Brunello in Montalcino and drive the Val d'Orcia
Val d'Orcia, Tuscany
A full day by carBook ahead
Brunello tasting in Montalcino, lunch in Pienza and cypress-lined lanes in late light: a slow day through the farmed hills south of Siena.
What it is
The Val d'Orcia, a UNESCO World Heritage site since 2004, is the farmed hill country south of Siena, and its wine town is Montalcino on the western edge, home of Brunello, made from 100% Sangiovese.
How to do it
There is no railway with regular service and buses between the towns are rare, so a car or a tour is the realistic option; Siena is about an hour's drive. A slow day: a morning tasting at a Montalcino estate booked ahead, lunch in Pienza, the town Pope Pius II rebuilt as an ideal Renaissance town, then the cypress-lined lanes around San Quirico d'Orcia in late light, ending at the hot-spring square of Bagno Vignoni.
Good to know
Whoever drives should taste and spit. Brunello is expensive; Rosso di Montalcino, from the same grape and released younger, is the bottle to drink with dinner.
Time needed
A full day by car
Best time
May to June, or September to October for the harvest
Siena is about an hour's drive north of the valley and Florence about two. The Via Cassia, the old road from Siena to Rome, runs through the middle past San Quirico and Bagno Vignoni. The nearest useful railway stations are Siena and Chiusi-Chianciano Terme, on the Florence to Rome line, from which you still need a car or a local bus.
Getting around
By car. Distances are short, Pienza to San Quirico is about 10 kilometres, but buses between the villages are rare and the best viewpoints are on country roads. The historic centres are limited traffic zones, so use the car parks below each town. Many farm stays and wineries sit on white gravel roads, which are fine at low speed.
How many days
In must30's view, two or three nights: one day for Pienza, Monticchiello and the Vitaleta chapel, one for Bagno Vignoni, Bagni San Filippo and Rocca d'Orcia, and one for Montalcino and Sant'Antimo. Add a morning in Montepulciano on the way in or out.
When to go
Late April to June, when the wheat is green and the poppies are out, and September to October, for the harvest and the gold stubble fields. Summer is hot and hazy at midday. Pienza holds its pecorino fair on the first Sunday of September, and the Teatro Povero plays in Monticchiello from late July to mid August.
Where to base yourself
Pienza and San Quirico d'Orcia are the most central towns, with restaurants in walking distance. A farm stay (agriturismo) in the countryside gives you the views at dawn and dusk but means driving to dinner. Montepulciano and Montalcino suit wine-focused trips at either edge of the valley.
Questions travellers ask
Can you visit the Val d'Orcia without a car?
Only partly. Buses between the villages are rare and there is no useful railway inside the valley, so a car or a guided tour from Siena or Florence is the realistic way to see more than one town in a day.
Can you swim in the hot springs of Bagno Vignoni?
Not in the pool in the village square, where bathing is forbidden. Below the village, in the Parco dei Mulini, warm water runs down channels and over the rock, where people soak their feet. For a full bath, the hotel spas in the village have thermal pools open to non-guests.
How do you get to the Vitaleta chapel?
It stands on private land off the road between San Quirico d'Orcia and Pienza. Follow the sign onto a short gravel road, park, and walk about a kilometre; walkers from Pienza can follow the back road from the parish church of Corsignano.
Is Montepulciano in the Val d'Orcia?
Just outside it. The town stands on the ridge between the Val d'Orcia and the Val di Chiana, a short drive from Pienza, and most visitors combine the two. Its wine is Vino Nobile di Montepulciano, made mainly from Sangiovese.
