The Val d'Orcia Itinerary

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There is a particular quality of light in the Val d'Orcia in the late afternoon — low and amber, falling across chalk-white hills and dark cypress rows — that stops you in the middle of whatever you were doing and makes you understand, without needing it explained, why this landscape has been painted, filmed, and written about for six centuries.

The Val d'Orcia is one of several days the province offers from a Siena base; Tuscany from Siena sets them beside each other.

The Val d'Orcia extends south of Siena across the agricultural hinterland of the province, following the Orcia river between the hills towards Monte Amiata. Since 2004 it has been a UNESCO World Heritage Site — a designation awarded not for any single monument, but for the landscape itself: the way wheat fields and olive groves and fortified villages on conical hills compose a picture that appears designed. It was, in a sense. The landscape as it unfolds nowadays was created as an investment by wealthy Sienese merchants in the 14th and 15th centuries. The farmers cultivated mainly grains, vines and olives, and had to share part of their revenue with the merchants as rent. The Val d'Orcia represents an exceptional example of how the landscape was transformed during the Renaissance to reflect the ideals of good governance and aesthetic research.

What this means for the visitor is a landscape of unusual coherence — one where the aesthetic decisions of seven hundred years of careful land management have produced something that feels simultaneously ancient and entirely alive. The farms are still farmed. The villages are still lived in. The wine from the surrounding hills is still among the finest produced anywhere.

This itinerary covers the Val d'Orcia over three days, moving through its principal towns and landscapes at a pace that allows genuine engagement rather than box-ticking. It is designed for those who want to understand what they are looking at.

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Before You Go: The Practicalities

Car is essential. There is no rail service through the Val d'Orcia. The historic line connecting Asciano to Monte Antico runs on selected dates using vintage steam engines — a wonderful experience to add if timing allows — but it does not provide practical access to the towns on this itinerary. Hire a car in Siena (car-hire links are in the Practical Information section below) and leave it at your hotel when you spend days in the city.

Base yourself strategically. Siena is the natural hub — 40 minutes from Montalcino, one hour from Pienza and San Quirico. A countryside estate in the Val d'Orcia itself — particularly around San Quirico or Montalcino — is an equally valid choice, particularly for the middle nights of this itinerary.

Distances are short; drive slowly. The SP146, running east from San Quirico d'Orcia through Pienza towards Montepulciano, is one of the most beautiful roads in Tuscany. Podere Belvedere — the farmhouse on its rise just outside San Quirico, on the right of the road — is among the most photographed landscapes on earth. Leave time to stop.

Season matters. The Val d'Orcia is beautiful in every season, but the quality of light and landscape shifts considerably. Spring (April–May) brings green hills and wildflowers. Harvest season (September–October) turns the vineyards gold and red. Winter reveals the bare chalk hills (crete) in their most dramatic form. Summer is warm and golden but busiest. The photographs you have seen were mostly taken in spring or autumn.

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Day One — Siena to Montalcino

Distance from Siena: 40km | Driving time: approximately 50 minutes via SS2 and SP45

Morning: The Drive South

Leave Siena via the SS2 — the Via Cassia — heading south towards Buonconvento. The landscape changes almost immediately beyond the city walls: the olive groves and vineyards of the Chianti Classico zone give way, south of Monteroni d'Arbia, to the clay hills of the Crete Senesi — a landscape of particular strangeness, pale and nearly treeless, punctuated by lone farmhouses and isolated cypress trees. This is the Val d'Arbia, the precursor to the Val d'Orcia proper, and worth slowing down for.

At Buonconvento, turn west on the SP45 through the Brunello vineyards towards Montalcino. The approach to the town through the vines, with the medieval fortress visible on its hill above, is one of the better arrivals in Tuscany.

Midday: Montalcino

Park below the walls and walk into the old town. Montalcino sits at 564 metres and has been a fortress since the Middle Ages — it was the last redoubt of the Sienese Republic after the city fell to the Medici in 1555, holding out until 1559, a fact the Sienese remember with pride to this day. A delegation from Montalcino still marches in the Palio corteo carrying the Republican flag.

What to do:

The Fortezza at the town's highest point houses both a municipal wine shop and views extending across the Val d'Orcia to the south and the Crete to the north. The enoteca inside is one of the most comprehensive places to taste wines from multiple Brunello producers side by side — a useful exercise before visiting individual estates.

The town's main street, Via Mazzini, is lined with shops selling Brunello, Rosso di Montalcino, local honey, and pecorino. It is short enough to walk end to end in fifteen minutes; the Musei di Montalcino, in the former convent of Sant'Agostino on Via Ricasoli, hold a collection of Sienese school paintings and sacred art worth thirty minutes of attention; they open daily from spring to early November and weekends only through the winter, so check ahead out of season.

Lunch: The Taverna dei Barbi, at Fattoria dei Barbi (10 minutes south of Montalcino), offers the most complete lunch in the area — estate wines, local cheeses, cold cuts, and traditional dishes in a setting that doubles as a cellar door. Book in advance.

Afternoon: Cellar Visits

Spend the afternoon at one or two estates. The most rewarding approach is to book a late afternoon tasting — between 3:30pm and 5:30pm — that allows the wine to be tasted in the cooler part of the day and the estate to be seen in the golden hour light. Le Potazzine (organic, artisan, small groups only, +39 0577 846168) or Fattoria dei Barbi are the strongest choices for a first visit to the zone. See our full guide to Brunello di Montalcino estates for the complete selection.

Evening: The Abbey of Sant'Antimo

Ten kilometres south of Montalcino, down a road that winds through vineyards into a valley of unusual quiet, stands the Abbey of Sant'Antimo — considered the most beautiful Romanesque church in Italy by a number of authorities, a claim that is difficult to dispute when you are standing in front of it. Founded in the 9th century, constructed in luminous travertine stone with Carolingian and Lombard decorative elements, it sits in its valley with a completeness and serenity that no photograph adequately captures.

The resident community of French Premonstratensian canons, long famed for the Gregorian chant sung at the daily offices, left in 2015, and no monastic community lives at Sant'Antimo today; the abbey is now cared for by the Archdiocese of Siena–Colle di Val d'Elsa–Montalcino, which holds worship and cultural events, with Gregorian chant performed on occasion rather than as a daily monastic office. Check the official abbey site for current service and chant times before planning an evening visit around them. Even so, arriving in the late afternoon, when the light enters through the alabaster windows, remains one of the most extraordinary experiences the Val d'Orcia offers.

Explore guided Val d'Orcia tours from Siena → (affiliate link — we may earn a commission at no cost to you)

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Day Two — San Quirico d'Orcia and Bagno Vignoni

Distance from Montalcino: 22km | Distance from Siena: 42km

Morning: San Quirico d'Orcia

San Quirico d'Orcia is the gateway town of the Val d'Orcia — the point at which the SP146, the great diagonal road that threads the valley, begins its journey east towards Pienza and Montepulciano. The town itself is small, walled, and possessed of a medieval dignity that the more visited towns of Tuscany have sometimes lost.

Just outside the city walls is the unmissable Collegiate Church of Saints Quirico and Giulitta, a Romanesque building whose first records date back as far as the 8th century. The church has three portals, one of which — facing Siena — is a splendid example of Romanesque design and its decor is a rare example of Lombard style in Tuscany. The first doorway is particularly remarkable and is credited to Giovanni Pisano.

Stand in front of this portal for a few minutes and study the stone carving — the animals, the crocodiles facing each other on the architrave, the figure of San Quirico in the lunette above. Craftsmanship of this quality, still standing in the open air after nine centuries, is not a thing to rush past.

From the church, walk the length of Via Dante Alighieri — the main street — to the Horti Leonini. Designed around 1540 by Diomede Leoni, the gardens have a beautiful statue of Cosimo III de' Medici in the centre. The geometric box hedging, the holm oak avenue, and the views down the hill towards the Val d'Orcia make this one of the most serene public gardens in Tuscany — and it is free to enter.

Midday: The Drive to Pienza via the Cypress Road

Leave San Quirico east on the SP146 towards Pienza. Just outside the town, on the right of the road, Podere Belvedere stands on its rise — a private farm, photographed from the roadside, and among the most reproduced images of Tuscany anywhere. Pull over properly. Photograph it in silence. It is as beautiful as advertised.

One correction worth carrying, because almost every guide repeats the error: the celebrated tree-lined avenue that visitors expect to find here is not Podere Belvedere's. The Comune di San Quirico places that avenue at Poggio Manzuoli, on the left of the same road. Both are located precisely in photographing the Val d'Orcia.

Continue east to Pienza. The arrival — through the town gates into a compact Renaissance piazza — is a transition from landscape to architecture of striking abruptness.

Afternoon: Pienza

Pienza is known for three things: its status as a UNESCO-designated Renaissance "ideal city" commissioned by Pope Pius II in the 15th century, its Pecorino di Pienza cheese made from local sheep's milk, and its sweeping views over the Val d'Orcia.

All three deserve proper attention.

Piazza Pio II is the heart of the town and one of the finest public spaces of the Italian Renaissance — the Cathedral, the Palazzo Piccolomini, the Palazzo Comunale, and the Bishop's Palace arranged around a trapezoid that Bernardo Rossellino designed in 1459 under Pope Pius II's explicit instruction. Pope Pius II decided to remodel Pienza according to his humanist beliefs, attempting to create the Ideal City, a Renaissance idea whereby one could attempt to mirror the perfection of heavenly proportions and layouts here, and thus also create a better society on earth. He charged Bernardo Rossellino with this quite daunting task. The Cathedral of Santa Maria Assunta, built after 1459, was subject to a Papal Bull forbidding changes — it has remained essentially unaltered since.

Palazzo Piccolomini is visitable and contains the pope's bedroom, library, and great hall, all preserved in their original state. The rooftop hanging garden — the first of its kind in Italy — surveys the Val d'Orcia below.

Pecorino di Pienza: The main street, Corso il Rossellino, is lined with small shops selling locally produced pecorino in every stage of maturation — from dolce (mild, young) to stagionato (aged and decisive). The cheese gets its special and notable flavour from three wild herbs that grow in the grassy hills outside of Pienza: artemisia, barberry, and minstrel. Buy some to take home. It travels well and opens a bottle of Brunello or Rosso beautifully.

Fiera del Cacio: On the first Sunday of September each year, Pienza hosts its Pecorino cheese fair — including a traditional cheese-wheel rolling contest. If your visit coincides, attend.

Late Afternoon: Bagno Vignoni

Return west from Pienza on the SP146 to San Quirico, then south five kilometres to Bagno Vignoni — one of the most singular villages in the Val d'Orcia, and one of the least expected.

Bagno Vignoni is a small and unique medieval village in Val d'Orcia: the centre of the village is dominated by the Piazza delle Sorgenti, a rectangular 16th-century tank, which contains a source of hot spring water that comes out steaming from the underground aquifer of volcanic origins.

What this means, in practice, is that the piazza — the central public space of the village — is a pool. Not a fountain, not a decorative feature, but a full Renaissance thermal pool that still steams in the cooler months. It is the most architecturally unexpected thing in the Val d'Orcia and worth seeing simply for its strangeness.

Over the centuries this has become the most famous spa in the Val d'Orcia. Bagno Vignoni's fame is testified by the frequentation of some of the illustrious personalities of the history of Tuscany. Among these are Pope Pius II, a native of nearby Pienza, Lorenzo de' Medici, the Magnificent, who used to retire to the baths of Bagno Vignoni to treat himself and study, and Santa Caterina da Siena who often went to Bagno Vignoni to pray alone.

In the 1980s, the Soviet director Andrei Tarkovsky chose Bagno Vignoni as the principal location for Nostalghia — the film that won the Grand Prix du cinéma de création at the 1983 Cannes Film Festival. The vapours rising from the thermal pool, the medieval stonework, and the surrounding landscape gave the film its quality of luminous, melancholy unreality. It is worth watching before visiting.

The modern spa facilities — the ADLER Spa Resort THERMAE has thermal swimming pools, sauna, steam bath, and treatment rooms — are available to day visitors as well as hotel guests. For those wanting to take the waters properly, an afternoon at the ADLER followed by dinner at one of the village's small restaurants is the right approach.

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Day Three — The Return via the Val d'Orcia Drive

The SP146 from Pienza west to Siena, with stops

The third day is best used for a slow return to Siena along the valley road, incorporating stops that the programme of the first two days may not have allowed.

Morning: Castiglione d'Orcia

North of Bagno Vignoni, Castiglione d'Orcia is the least visited of the Val d'Orcia's principal villages and arguably the most authentically medieval in atmosphere. Perched on a hill, Castiglione d'Orcia dominates the landscape with the suggestive ruins of the Rocca degli Aldobrandeschi. The village, crossed through, preserves its medieval charm with stone alleys and long views over the valley.

Rocca d'Orcia — a hamlet directly below Castiglione, built around its own tower — is worth the five-minute diversion. From here the view down the valley, with the thermal vapours of Bagno Vignoni visible in the middle distance and Monte Amiata on the southern horizon, is among the most complete panoramas in the area.

Midday: The Crete Senesi

The route north from San Quirico through Asciano passes through the Crete Senesi — the bare, undulating clay hills that give southern Tuscany its distinctive lunar quality. In the words of the landscape geographers: chalk plains out of which rise almost conical hills with fortified settlements on top. In spring, when the cereal crops turn the hills green, the light in the Crete is extraordinary. In winter and early spring, after the harvest, the bare clay has the quality of a minimalist painting.

The hamlet of Lucignano d'Arbia is barely a stop, but the drive through these hills — particularly on the SP438 between Asciano and Siena — is among the most quietly beautiful in the province.

Afternoon: Return to Siena

Allow yourself to arrive back in Siena by late afternoon, in time for aperitivo at one of the bars along Via Banchi di Sopra or on the Campo itself. The transition from the vast silence of the Val d'Orcia to the compressed medieval energy of Siena is, in its own way, as affecting as the landscape you have spent three days in.

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Where to Stay in the Val d'Orcia

Several estates and country hotels in the Val d'Orcia allow you to base yourself within the landscape rather than driving in from Siena each day.

Podere Brizio, Montalcino — A boutique vineyard estate 10 minutes from Montalcino, set in a southwest-facing valley among olive groves. Accommodation in converted farmhouse apartments alongside the winery, with tastings on site. Well-positioned for Day One of this itinerary.

ADLER Spa Resort THERMAE, Bagno Vignoni — For those whose priority is the thermal spa experience alongside landscape. The resort is set in the Val d'Orcia itself, with thermal pools fed by the same volcanic springs as the village piazza, and zero-kilometre dining.

For a full overview of the finest hotels in the wider Siena area, including Belmond Castello di Casole (20 minutes from Siena), see our complete luxury hotel guide.

Search hotels in the Val d'Orcia → (affiliate link)

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Practical Information

Getting around: All distances in the Val d'Orcia are short by Tuscan standards — no town on this itinerary is more than 30 minutes from another by car. The SP146 between San Quirico and Pienza is the most scenic road and doubles as the main tourist route; in high summer, it can be slow on weekends. Hire a car in Siena (affiliate link) if you are not collecting one at the airport.

Photography: The most-photographed location is Podere Belvedere, on the right of the SP146 just outside San Quirico, best at dawn with fog in the folds below — and the famous avenue nearby belongs to Poggio Manzuoli, on the left (all of them, located). Pienza's southern wall, with the Val d'Orcia below, photographs well at any time. Sant'Antimo in the late afternoon light is exceptional.

Food and wine: Bring a cool bag in summer. The combination of Brunello from Montalcino, pecorino from Pienza, local honey, and salumi makes the best hamper in Tuscany. Local markets — San Quirico on Thursdays, Pienza on Saturdays — supply everything.

Steam train: The Ferrovia Val d'Orcia — a vintage and steam train service connecting Asciano and Monte Antico — runs on selected dates between March and December, typically linked to local food festivals. Check the Trenitalia regional website for the current season's dates. It is primarily a scenic and experiential service rather than a transport solution, and one of the more memorable additions to a Val d'Orcia itinerary if the dates align.

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Frequently Asked Questions

What is the Val d'Orcia? The Val d'Orcia is a valley in southern Tuscany extending from the hills south of Siena to Monte Amiata. It was inscribed as a UNESCO World Heritage Cultural Landscape in 2004, recognised for its exceptional Renaissance agricultural landscape and its influence on Western art. It includes the towns of Pienza, San Quirico d'Orcia, Montalcino, Castiglione d'Orcia, and Radicofani.

How far is the Val d'Orcia from Siena? The nearest towns of the Val d'Orcia — San Quirico d'Orcia and the turning for Bagno Vignoni — are approximately 42 kilometres from Siena, around 45 minutes by car on the SS2 south. Montalcino is 40 kilometres, Pienza approximately 50 kilometres.

Do I need a car to visit the Val d'Orcia? Yes. There is no practical public transport linking the Val d'Orcia's principal towns. Guided tours from Siena are a good alternative for those who prefer not to drive. There is a vintage steam train service on selected dates, but it does not connect the towns covered in this itinerary.

What is Pienza famous for? Pienza is the Renaissance "ideal city" commissioned by Pope Pius II in the 15th century, a UNESCO World Heritage Site in its own right since 1996. It is also celebrated for Pecorino di Pienza — a sheep's milk cheese with PDO (Protected Designation of Origin) status, sold throughout the town in various stages of ageing.

What are the hot springs at Bagno Vignoni? Bagno Vignoni is a medieval hamlet in the municipality of San Quirico d'Orcia, built around a 16th-century thermal pool fed by volcanic hot springs at approximately 49°C. These springs have been in use since Roman and Etruscan times; Pope Pius II, Lorenzo the Magnificent, and Saint Catherine of Siena all bathed here. The village was the principal location of Andrei Tarkovsky's 1983 film Nostalghia.

When is the best time to visit the Val d'Orcia? Spring (April–May) for green hills and wildflowers; harvest season (September–October) for the vendemmia and autumn colours; winter for the dramatic bare clay hills of the Crete Senesi and the absence of crowds. Summer is beautiful but the most visited period.

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Sources: UNESCO World Heritage Centre (whc.unesco.org), Parco della Val d'Orcia official website (parcodellavaldorcia.com), Visit Tuscany official (visittuscany.com), Italia.it official Italian tourism portal, Bagno Vignoni, Pienza, Discover Tuscany (discovertuscany.com), Bella Toscana (bella-toscana.com), Summer in Italy (summerinitaly.com).

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