When most people think of Tuscan wine, they think of Chianti. That is understandable. Chianti Classico is one of Italy’s most exported and internationally recognised appellations, and the rolling hills between Florence and Siena have been photographed so many times that they function as a visual shorthand for the entire region. We have written about Chianti already, and it deserves every word. If you havent seen it, click here to read.
Even though Chianti is the northern entry point to a wine map that extends much further south, in the Val d’Orcia, on the slopes around Montalcino and Montepulciano, along the Maremma coast there are, by any objective measure, among the most complex, prestigious, and age worthy red wines produced anywhere on earth.
If you have not yet explored southern Tuscany’s wines, this is where to start.
The landscape: Val d’Orcia and why it matters
The Val d’Orcia is a wide, shallow valley in the province of Siena, designated a UNESCO World Heritage Site in 2004. It is an honour given not to an ancient monument but to an agricultural landscape, on the basis that the scenery of rolling hills, cypress avenues, stone farmhouses, and medieval hilltop towns is itself a cultural artefact of outstanding universal value. The painters of the Sienese school used this countryside as their background in the 14th and 15th centuries, and the landscape they depicted has changed remarkably little since.
It is also, not coincidentally, some of the finest wine growing territory in Italy. The combination of clay and limestone soils (called tufo and galestro), the altitude of the hilltop towns that elevates vineyards between 250 and 600 metres above sea level, and the continental climate with warm days and cold nights during the growing season creates conditions ideally suited to the slow, even ripening of Sangiovese.
The same grape that makes Chianti Classico in the north produces something distinctly different here: more concentrated, more structured, more capable of long ageing, and with a mineral depth that reflects the specific geology of this valley.
Brunello di Montalcino DOCG: Italy’s prestigious red wine
Montalcino is a small medieval town on a hill in the southern Val d’Orcia, its 14th century castle visible for miles across the surrounding countryside. For most of its history, it was known locally for the quality of its wine and ignored by the wider world. That changed in the second half of the 19th century when Ferruccio Biondi-Santi identified a particular clone of Sangiovese growing on his estate that he called Brunello, meaning “the little dark one,” for the deep colour of the grape skins. He decided to use it for wine and released a wine in 1888 that bore no resemblance to anything being produced in Tuscany at the time.
Montalcino’s vineyards are divided broadly between the northern slopes: higher altitude, cooler temperatures, producing wines of greater elegance and acidity.
On the other hand the southern lies toward Sant’Angelo in Colle, lower and warmer, producing richer and more immediately approachable styles. Understanding this north and south division inside a single area is one of the things that separates a Brunello enthusiast from a casual drinker, and a good guided wine tour will explain it with a glass in your hand.
When we discuss about the wines of South Tuscany, we can talk about also Rosso di Montalcino DOC (which are from the same grapes but a different timeline), Vino Nobile di Montepulciano DOCG (the wine that gets its name from the nobles), Morellino di Scansano DOCG (the wine of Sangiovese reaches the sea and having a touch of the sea breeze in its taste). We can totally say that Tuscany is a gem for a good wine.
The food that belongs alongside these wines
No southern Tuscany’s wines is complete without its food. The Pecorino di Pienza is produced in this region. It is a sheep’s milk cheese aged in anything from a few weeks to several months, rubbed with olive oil, ash, tomato, or walnut leaves during ageing to produce a range of flavours that pair with southern Tuscany’s wines as precisely as anything the region produces. The combination of aged wine and Pecorino di Pienza is one of those food and wine pairings that makes immediate, complete sense the first time you encounter it.
How to experience southern Tuscany’s wines properly
The Val d’Orcia rewards the unhurried approach. From Siena, the full arc of Montepulciano, Pienza, and Montalcino can be covered in a single full day. A traditional Tuscan lunch in Montepulciano with red wine and Vino Nobile paired, then having a stroll in Pienza’s Renaissance streets, and finally a guided winery tasting in Montalcino where the Brunello ageing cellars make the investment of time and patience visible in a way that no description manages.
It is a beautiful day, isn’t it? and it is not a dream but an ongoing tour we offer to the wine enthusiasts coming to Tuscany to experience those first hand.
👉 Book the Best of Tuscany Wines & Lunch in Montepulciano from Siena →

