Val d’Orcia is not just “pretty countryside”. Since 2004 it has been listed as a UNESCO World Heritage Site as an example of a designed agricultural landscape: hills, farmhouses, cypress lines and small towns all shaped deliberately, over centuries, to balance beauty, productivity and human scale.
Those familiar views between Siena and Montepulciano are not an accident. They are the result of careful decisions about where to plant vines and olives, how to terrace fields, where to build roads and how to frame the horizon – choices that still define how you experience the area today.
A single cypress, two walkers and miles of soft green curves to frame the silence.
Where Val d’Orcia Sits in the Wider Tuscany
Between Siena and Montepulciano lies a band of hills where the pace drops and the sky seems to expand. Give this area five to seven nights and it becomes something more than a scenic drive: the stretch of your holiday where you actually live in Tuscany for a while.
Within the region as a whole, it plays a very specific role:
Compared with Chianti, you still have vineyards and good food, but the landscape opens out. Here you see more fields and clay ridges, lone farmhouses and chapels, wider horizons. Wine is part of the story, alongside hot springs, gardens, walking and small-town life.
Compared with the Tuscan coast, you lose the sea but gain a sense of depth and stillness. The coast can be the other half of a “sea + hills” itinerary; Val d’Orcia comfortably stands alone as the inland segment, without depending on Florence or Chianti to justify the journey.
It is, in short, the Tuscany you choose when you care as much about space and atmosphere as about individual “sights”.
The kind of cypress-lined drive you imagine long before you ever see it in person.
Crete Senesi and Brunello: One Well-Spent Wine Day
South and south-east of Siena the land drops into the Crete Senesi – pale clay hills, sculpted folds and solitary farms – before rising again towards Montalcino and the Brunello vineyards. The old roads through Asciano and Buonconvento, and the disused Asciano–Monte Antico railway, give some of the most characteristic inner-Tuscany views in a single sweep.
For wine-minded travellers, this is the natural arena for a Brunello day: one well-chosen estate visit, perhaps a shorter second tasting, and time left over for a pause in Montalcino itself. It is less about ticking off labels and more about linking the countryside, the cellar and the glass in your own mind.
Clay ridges, cypress lines and fields the colour of straw – Tuscany reduced to pure pattern.
Montalcino keeps watch over the Val d’Orcia, its towers rising above olives, vines and tiled roofs.
Fattoria dei Barbi – A Classic Brunello Estate
What it is: One of Montalcino’s historic Brunello producers, owned by the Colombini family for centuries and bottling Brunello since the late 19th century. Fattoria dei Barbi combines a working estate with an historical bottle cellar, a small Brunello museum and an on-site Taverna.
Why it matters: A visit here gives a rounded sense of Brunello in one place – vineyards, ageing cellars, family history and current production – without feeling stage-managed. It is a useful reference point, whether or not you then visit smaller or more experimental wineries.
What to expect:
⚫ A walk through the barrel cellars and the historic bottle archive.
⚫ A guided tasting of several wines (typically including Brunello and Rosso di Montalcino), with time to ask questions rather than just taste and leave.
⚫ Optional access to a compact Museo del Brunello, covering the development of the wine and territory.
⚫ The Taverna dei Barbi, serving traditional dishes that sit naturally alongside the estate wines.
ExpertoItaly note: Many itineraries use Fattoria dei Barbi as the main “structured” visit of a Brunello day, leaving additional time simply to enjoy Montalcino or the Crete Senesi viewpoints on the way back.
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San Quirico d’Orcia: A Village That Still Belongs to Itself
San Quirico d’Orcia waking up slowly, stone and cypress wrapped in soft morning light.
San Quirico d’Orcia sits roughly halfway between Siena and Montepulciano, on the line of the old Via Francigena. It feels less like a stage set and more like a place that still works for its residents: a compact main street, a couple of churches, a square where children play and older neighbours sit in quiet conversation.
A short circuit is enough to understand it. Follow the main street towards Piazza della Libertà, step into the Collegiata dei Santi Quirico e Giulitta, then continue to the small Santa Maria Assunta, once surrounded by vegetable plots, with the former pilgrim hospital opposite. Slip into the gardens of Horti Leonini, then circle back towards the walls.
San Quirico is at its best when you let it be ordinary: coffee at the bar, a plate of salumi and Pecorino in a contemporary wine-and-grocery shop, a few minutes on a bench simply watching who comes and goes. It also happens to be one of the most efficient bases for reaching Pienza, Bagno Vignoni and the classic viewpoints in all directions.
One turn off the main road and San Quirico d’Orcia feels instantly, disarmingly local.
A perfect ring of cypresses in the fields above San Quirico – geometry drawn straight onto the landscape.
Horti Leonini – San Quirico’s Renaissance Garden
What it is: A late 16th-century Italian garden, created by Diomede Leoni on land granted by the Medici, set into the bastions of San Quirico d’Orcia and conceived from the outset as a public green space rather than a private villa garden.
Why it matters: The lower level is a formal giardino all’italiana – clipped box hedges in strict geometry around a statue of Cosimo III de’ Medici – while the upper level opens into a more natural, wooded area and a small rose garden. It is a compact illustration of how Renaissance order and the surrounding countryside were made to work together.
Visiting notes:
⚫Admission is usually free, with access in daylight hours from morning to late afternoon or early evening.
⚫Twenty to forty minutes suffice for a slow walk along the central avenue, a circuit of the parterre and a look from the upper lawn.
⚫At certain times of year the garden hosts temporary sculpture and cultural events; if something is on, it simply adds another layer to the visit.
ExpertoItaly note: The garden works well either at the start of a San Quirico stroll – to set the tone – or at the end, as a calm pause before dinner.
Step through the shade and Horti Leonini opens up in front of you, all geometry, light and quiet.
Bagno Vignoni and Its Thermal Waters
A window of stone onto Bagno Vignoni’s steaming pool, where water has shaped village life for centuries.
A village built around a pool
Seen from above, Bagno Vignoni barely qualifies as a village: a handful of stone houses, an oratory, a small square. What makes it remarkable is the large rectangular pool at its centre, constantly steaming, fed by the same hot springs that have drawn people here for centuries.
From Romans and pilgrims to Renaissance visitors
The Romans already knew these waters. In the Middle Ages and Renaissance, Bagno Vignoni became an important stop on the Via Francigena, the pilgrimage route between northern Europe and Rome. Travellers, merchants, clerics and nobles used the baths to rest aching bodies on their way south; for them, the water was both a remedy and a social meeting point.
The historic pool today
The historic pool in the main square is no longer used for bathing. It survives as a striking open-air basin, edged by stone façades and watched over by the small church of San Giovanni Battista. The water still rises hot – around 49–52 °C – and spills towards the edge of the village, where it once powered a line of mills cut into the rock in the Parco dei Mulini below.
Where you actually bathe now
Today, bathing takes place in modern pools and spa facilities that tap into the same springs. For a complete thermal experience rather than a token dip, many travellers dedicate one whole day to a spa complex such as Adler Spa Resort Thermae, just outside the hamlet, where the water is cooled to a comfortable 36–38 °C and the pools look straight out onto the surrounding hills.
Bagno Vignoni Spa Day at Adler – How It Works
Where: Adler Spa Resort Thermae, just outside the historic hamlet of Bagno Vignoni, Val d’Orcia
When: Day spa access typically from 08:00 to 20:00
Day spa prices (guide):
€177 per person – midweek day spa
€199 per person – weekend day spa (Friday–Sunday)
What is included:
⚫ Full-day access to indoor and outdoor thermal pools (around 36 °C)
⚫Use of saunas, steam rooms and quiet relaxation areas
⚫ Access to the Grotta Salina (salt grotto pool at approx. 38 °C, by reservation)
⚫ One 50-minute massage per person
⚫ Afternoon buffet of cakes and fresh fruit
ExpertoItaly note: Many guests use this as a “centre of gravity” day in the middle of their stay, giving themselves permission to do nothing more demanding than move between water, heat, treatment room and a good book.
Pienza: Stone, Light and Pecorino
From this terrace, Pienza feels both tucked into its gardens and completely open to the Val d’Orcia.
A small town drawn with a ruler and an eye for light
Pienza is compact and carefully planned, one of the clearest examples of Renaissance ideas applied to a real town. Piazza Pio II, the cathedral and Palazzo Piccolomini were conceived together so that architecture, light and landscape form a single composition. Step into the square and the calm proportions and deliberate views are immediately obvious.
How long to allow
You do not need a full day here. Three to four hours are usually enough to see the principal spaces, enjoy a proper Pecorino tasting and, if you wish, add a palace visit or a dairy picnic.
Start with the terrace
Begin in Piazza Pio II, take a few minutes inside the cathedral, then walk behind it to the terrace. The view over the Val d’Orcia is wide and layered; once you have seen it, the rest of your time in the valley gains a frame.
Pecorino with context
Rather than grazing from counter to counter, many visitors prefer to anchor their experience in a single, well-chosen cheesemonger or at a dairy just outside town, tasting Pecorino in a short sequence from young to aged. It is a very efficient way to discover what you actually like, instead of collecting random samples.
People, craft and gelato
A couple of stops in real workshops – where the maker is also the person behind the counter – are enough to connect Pienza to a human story: textiles, ceramics, leather or wood, depending on what catches your eye. A final gelato from a seasonally minded gelateria, with a shorter list and one or two flavours “just for now”, ends the visit gently.
Palazzo Piccolomini – Pienza’s Renaissance Palace with a View
What it is: The 15th-century palace commissioned by Enea Silvio Piccolomini (Pope Pius II) as his summer residence, built as part of the “ideal city” project that reshaped Pienza. Today it is a museum with furnished rooms and a hanging garden overlooking the Val d’Orcia.
Why it matters: Palazzo Piccolomini shows how architecture, light and landscape were designed together. The sequence of courtyard, rooms and garden frames one of the most recognisable views of the valley and Mount Amiata, and illustrates why UNESCO treats this as a cultural landscape rather than simply attractive countryside.
Visiting notes:
⚫ Entry is normally by timed visit, with a set route through the main rooms and access to the hanging garden.
⚫ Photography is often restricted inside; pictures are usually allowed only in the courtyard and garden.
⚫ Allow around 45–60 minutes, which folds neatly into a wider Pienza visit.
Picnic with a View at Caseificio Cugusi
What it is: A long-established family dairy between Pienza and Montepulciano, producing Pecorino and offering outdoor tastings and picnics with views towards Montepulciano and the Temple of San Biagio.
Why go: It is one of the most direct ways to connect Pecorino with its landscape: cheeses from the dairy’s own milk, local salumi and bread served in a picnic area facing the hills, with wine from Montepulciano and often craft beer available.
What to expect:
⚫ An outdoor picnic area with simple tables and open views.
⚫ Tasting plates or picnic baskets featuring several Pecorini, cured meats and accompaniments.
⚫ Local wines and beers by the glass or bottle.
⚫ Service geared to the warmer months, when it is pleasant to sit outside.
Montepulciano and Monticchiello: Two Edges of the Landscape
Montepulciano – height, alleys and Vino Nobile
Montepulciano occupies a long ridge, its main street climbing towards Piazza Grande and the cathedral. Beneath the surface, a network of historic cellars runs through the tufa and brick. A few hours are enough to see the square, glance into the Duomo, visit one of the major cellars and taste Vino Nobile di Montepulciano and Rosso di Montepulciano with something small to eat.
The town’s position means you are rarely far from a view: along the ridge street you repeatedly look down over the patchwork towards the Val d’Orcia on one side and the lakes and Umbrian border on the other.
Monticchiello – small, quiet, looking out
Monticchiello is the opposite in scale: a tiny walled village whose streets you can walk in minutes, but which offers one of the cleanest outward views across the valley. A short path just beyond the walls allows you to step back and see village and landscape together. A lunch or early supper here easily turns into one of the quietly memorable episodes of a stay.
One track, two names on the signpost – Pienza ahead, Monticchiello just around the curve.
Treno Natura: Historic Railway Through the Val d’Orcia
Treno Natura – Steam Railway Days from Siena (2026)
What it is: A full-day steam train excursion on the historic Asciano–Monte Antico line, running in a ring from Siena – Monte Antico – Asciano – Siena for about 148 km.
The train is made up of an early 20th-century steam locomotive and five 1930s “Centoporte” carriages,each with around 78 seats, restored for heritage travel rather than speed.
On board: live music in some coaches, volunteers from the Val d’Orcia railway association, a guide giving commentary on the line and landscape, and an environmental guide for short organised walks (usually up to 7 km) at the various stops. It is a slow, convivial way to cross the Crete Senesi and the Val d’Orcia, rather than a simple transfer.
How the day works: departures are from Siena, with return to the same station in the late afternoon. The train stops for village festivals, food fairs and local markets, giving time to visit, taste and walk before re-boarding. On some dates a short coach transfer links the station with the hill town hosting the event.
2026 programme – spring departures:
• 15 March (Sunday) – San Giovanni d’Asso: “Treno del Tartufo Marzuolo”, dedicated to early spring truffle in the Crete Senesi.
• 6 April (Monday) – Buonconvento: regional antiques fair “Cose del Passato”, with stalls and collectors throughout the village.
• 25 April (Saturday) – Castiglione d’Orcia: “Primavera in Val d’Orcia”, spring festival with a short coach link from the station.
• 1 May (Friday) – Sant’Angelo Scalo / Montalcino: “La Maggiolata”, welcoming spring in Brunello country.
• 10 May (Sunday) – Asciano: “Alla scoperta delle Crete Senesi”, food and traditions of the clay hills.
• 17 May (Sunday) – Torrenieri / Montalcino: “Festa del Treno”, celebrating the history of the railway itself.
• 2 June (Tuesday) – Asciano: “Tra Crete e Tartufo”, focusing on Crete Senesi produce and local truffles.
2026 programme – autumn departures:
• 27 September (Sunday) – Chiusi: “Festa dell’Uva e del Vino”, grape and wine festival from Etruscan times to today.
• 10 October (Saturday) – Abbadia San Salvatore: “Festa d’Autunno”, village autumn fair in the old borgo, with bus transfer from the station.
• 11 October (Sunday) – Vivo d’Orcia / Castiglione d’Orcia: “Sagra del Fungo Porcino” and autumn fair, again with local transfers.
• 18 October (Sunday) – Trequanda: “Festa dell’Olio Novo”, celebrating new olive oil.
• 25 October (Sunday) – Montalcino: “Sagra del Tordo”, historic festival in the home of Brunello.
• 8 & 15 November (Sundays) – San Giovanni d’Asso / Montalcino: white truffle fair “Mostra Mercato del Tartufo Bianco”.
6 December (Sunday) – Siena (from Grosseto): day at the “Mercato nel Campo” in Piazza del Campo, with an optional coach link back to Grosseto.
Indicative prices: adults around €54, young people 11–18 years around €43, children up to 10 travel free (no reserved seat, normally one child per paying adult). Exact fares and booking conditions are set by the organisers and their partner agency in Siena.
Eroica Gravel & the Via Francigena
Cycling the Eroica Routes – Strade Bianche Through Val d’Orcia
What it is: L’Eroica is a vintage-cycling movement built around historic bikes, white gravel roads (strade bianche) and the landscapes south of Siena. Beyond the famous annual event there is a permanent route of about 209 km linking Chianti, the Crete Senesi and Val d’Orcia, with long stretches on unpaved roads and around 3,800 metres of climbing.
Why it matters here: Several Eroica variants, including Eroica Montalcino, pass directly through the Brunello country and Val d’Orcia, using classic gravel sectors between Siena, Montalcino and the Orcia valley. For experienced cyclists, riding sections of these routes is one of the most direct ways to feel the texture of the landscape: gradients, wind, dust, shade – not just views from behind a windscreen.
How it works in practice: The permanent itineraries can be ridden all year round, in whole or in sections, and are supported by local organisations and bike-tour companies that provide GPX tracks, gravel bikes, logistics and luggage shuttles. You do not need to join the main event to experience the route; many cyclists simply incorporate one or two key sectors into a wider Val d’Orcia or Brunello stay.
ExpertoItaly note: For guests already comfortable with long days and gravel, we can help identify which Eroica stretches fit naturally around your base – for example near Montalcino or between the Crete Senesi and Val d’Orcia – and coordinate bike hire and support through trusted local partners.
The Via Francigena Through Val d’Orcia – San Quirico to Radicofani
What it is: The Via Francigena is the historic pilgrimage route from Canterbury to Rome. In Tuscany it runs for almost 400 km, and one of its most scenic and demanding stretches is the section crossing Val d’Orcia from San Quirico d’Orcia, via Bagno Vignoni and Castiglione d’Orcia, to Radicofani.
The Val d’Orcia stage: The classic San Quirico–Radicofani section is roughly 33 km and usually described as one of the tougher Tuscan stages: rolling hills, long exposed stretches, the detour down to Bagno Vignoni’s thermal basin and the final climb towards Radicofani and its fortress. It is also one of the most representative: you move through the UNESCO agricultural landscape at walking pace, with time to register field patterns, cypress clusters and isolated farms.
Shorter variants: Many walkers break the Francigena here into shorter legs – for example San Quirico d’Orcia–Bagno Vignoni–Castiglione d’Orcia – or use local loops that follow the Francigena alignment for a while before circling back. Waymarking is generally good, and there is no shortage of mapping resources and GPX tracks if you prefer to prepare routes in detail.
Gravel beneath your wheels, empty hills ahead and the Val d’Orcia sky for company.
An Eroica-style morning: tyres humming on gravel, olive trees and cypresses marking the way.
Putting Val d’Orcia in the Picture
Once you know what sits between Siena and Montepulciano – the hot water of Bagno Vignoni, the Renaissance grid of Pienza, the gardens and lanes of San Quirico, the Crete Senesi and Brunello country, Montepulciano, Monticchiello, the Francigena and the gravel roads of L’Eroica – the map stops being abstract.
From there, it is simply a question of emphasis. More spa or more cellar? More walking or more time at a favourite table? A self-contained week in the hills, or a quieter inland chapter between a city and the sea.
The landscape has been designed over centuries to balance beauty and usefulness. Your task is only to decide which parts of that design you want to lean into.
Talk to us about a Val d’Orcia Holiday
With ExpertoItaly, your Val d’Orcia stay is never a template. We start from where you want to land – Siena, Rome, Pisa, the Tuscan coast – and build outwards, using a small number of tested bases between Siena and Montepulciano.
From there we connect the pieces you have just read about: thermal days in Bagno Vignoni, Brunello estates that are worth your time, Eroica gravel stretches or Francigena walks that fit your legs, dairies and picnics that feel local rather than staged – always with realistic driving times and transfers.
Our holidays are land-only and fully tailor-made: you tell us when you are coming, how you like to travel, and whether this should be a self-contained week in the hills or part of a wider Tuscany journey.
You’re in good hands
Clients often mention what matters most — care, precision, and the sense of travelling with someone who knows the way.
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