Val di Chiana: Tuscany's Quietest Valley

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Between the Val d'Orcia's cypress avenues and the Chianti hills lies a valley most itineraries skip entirely — flatter, less photographed, and considerably quieter, but home to the cattle behind Italy's most famous steak, a wine town rivalling Montalcino, and a hilltop settlement the Etruscans built almost three thousand years ago.

The Val di Chiana straddles two provinces — Arezzo to the east, Siena to the west — and stretches into Umbria at its southern edge. This guide focuses on the Sienese side, where most of the valley's wine and thermal towns sit, with Cortona treated as the essential extension worth crossing the provincial line for.

Montepulciano: Vino Nobile's Home

The valley's most significant town for anyone who already knows Brunello or Chianti Classico. Montepulciano sits on its own ridge above the valley floor, its historic centre built almost entirely from the wine trade that still defines it: Vino Nobile di Montepulciano, a DOCG red made primarily from Sangiovese (locally called Prugnolo Gentile), aged in extensive underground cellars carved into the volcanic tuff beneath the town.

Those cellars are the town's signature experience — several producers offer tastings directly in cavernous, centuries-old cantine rather than a modern tasting room, among the more atmospheric wine experiences in the region. The climb up the town's main street, the Corso, rewards with a view over both the Val di Chiana and the Val d'Orcia from the piazza at the top, where the Duomo sits.

Chianciano Terme, Chiusi & the Quieter Towns

Chianciano Terme, one of Italy's most established spa towns, draws on thermal waters with a history of medicinal use stretching back to Etruscan and Roman times — a different, more clinical spa tradition than Bagno Vignoni's, oriented toward extended wellness stays rather than a single day-spa visit.

Chiusi, on the valley's western edge near its namesake lake, holds some of the richest Etruscan archaeology in the region — an important museum and a genuine concentration of Etruscan tombs, evidence that this was a major Etruscan centre long before Rome's rise. Sarteano, nearby, punches above its size with its own significant Etruscan tombs and a 17th-century theatre. Cetona, Sinalunga, Torrita di Siena, and Trequanda round out the smaller hill towns worth a stop rather than a dedicated trip — quiet, largely untouristed, and a genuine contrast to the crowds further north in Chianti or San Gimignano.

Torrita di Siena is worth timing a visit around if possible: its Palio dei Somari — a donkey race through the town's streets on the feast of St Joseph (19 March), contested by its own historic districts <!-- check-terminology-ignore: Torrita di Siena's Palio dei Somari, not Siena's contrade; the correct term for Torrita's districts is not verified at source --> — is a smaller, less crowded cousin of the Palio spirit, genuinely local rather than staged for visitors. (The valley's celebrated barrel-rolling race, the Bravìo delle Botti, belongs to Montepulciano, on the last Sunday of August.)

Cortona: The Valley's Anchor

Technically in Arezzo province rather than Siena, Cortona is nonetheless the Val di Chiana's best-known and most rewarding stop, perched 500 metres up on Monte Sant'Egidio with sweeping views across the entire valley toward Lake Trasimeno. Etruscan-founded, the town holds its history visibly — ancient walls, the MAEC (Museum of the Etruscan Academy and of the City of Cortona), and cobbled medieval streets that climb steeply enough to make the panorama from the top feel earned.

Frances Mayes' memoir Under the Tuscan Sun — and the film it inspired — brought Cortona a level of international recognition disproportionate to its size, and the crowds around Piazza della Repubblica reflect it in high season. They thin quickly once away from the main squares, and the town rewards the extra half-hour of wandering that most day-trippers skip.

Cortona has also become, distinctively, Italy's centre of Syrah production — an unusual grape choice for Tuscany, pioneered locally by the D'Alessandro family and now recognised under the Cortona DOC. Molesini, a long-established wine shop on Piazza della Repubblica, is the easiest single stop for tasting across both Cortona's own wines and the wider valley's output.

The Food: Chianina Beef

The valley's defining culinary export is the Chianina — a striking, cream-coloured breed of cattle native to this exact stretch of Tuscany, and the source of true bistecca alla fiorentina: a substantial T-bone, grilled rare over an open fire, seasoned with little beyond salt, pepper, and olive oil. Nearly every trattoria in the valley serves some version of it, typically sized to share between two. Alongside the steak, expect wild boar stew, pici pasta in meat ragù, and — around Montepulciano specifically — Vin Santo, the traditional dessert wine served with cantucci biscuits.

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Getting Around

A car is genuinely necessary here — more so than almost anywhere else covered in our guides. Public transport connects the towns loosely at best, and the valley's real appeal (small-town squares, roadside wine cantine, viewpoints with no queue) depends on being able to stop wherever looks worth stopping. For a car-free alternative, the Sentiero della Bonifica is a flat, traffic-free 62km cycling and walking trail following the old reclamation canal from Arezzo down to Chiusi — a genuinely different, slower way to see the valley floor.

Practical Information

Distance from Siena: Montepulciano is roughly 65km (under an hour); Chiusi and the southern towns are somewhat further; Cortona is furthest at around 70–75km.

Best time: spring and autumn for sightseeing and driving between towns; summer suits a countryside stay with a pool more than a day of town-hopping in the heat.

How long to allow: Montepulciano alone deserves a half-day for its cellars; Cortona similarly. Combining both in one day is possible but rushed — better split across two days if time allows, ideally based from a countryside stay rather than commuting from Siena each day.

Pairing with Val d'Orcia: Montepulciano and Pienza sit close enough to the valley's western edge that combining a Val di Chiana day with a Val d'Orcia one is straightforward — see our Val d'Orcia itinerary for the western half of the same trip.

Continue Reading

• The Val d'Orcia Itinerary
• Best Brunello di Montalcino Wineries
• Tuscany's Thermal Springs: Bagno Vignoni & San Casciano dei Bagni

Frequently Asked Questions

Is Cortona in Siena province? No — Cortona is in Arezzo province, but it's close enough to the Val di Chiana's Sienese towns (Montepulciano, Chianciano Terme, Chiusi) to combine naturally in one trip.

What is Vino Nobile di Montepulciano? A DOCG red wine made primarily from Sangiovese (locally called Prugnolo Gentile), produced around Montepulciano and aged in extensive underground cellars carved into the town's volcanic tuff.

What is Chianina beef? A distinctive cream-coloured cattle breed native to the Val di Chiana, prized for its firm, flavourful meat and the source of authentic bistecca alla fiorentina.

Do I need a car to visit the Val di Chiana? Yes, effectively — public transport between the valley's towns is limited, and much of the area's appeal depends on stopping freely at small towns and roadside wineries.

How does the Val di Chiana compare to the Val d'Orcia? The Val di Chiana is flatter, less photographed, and considerably quieter than the Val d'Orcia's famous cypress-lined hills — better suited to travellers looking for wine towns and Etruscan history over the classic postcard landscape.

By the Siena & Toscana editors