Montepulciano, Montalcino and Pienza: The Val d'Orcia at Its Greatest

The Val d'Orcia is the landscape that defines the popular image of Tuscany. The three towns at its heart — Montalcino, Montepulciano and Pienza — produce between them two of Italy's greatest red wines and one of its finest cheeses. We design the itinerary that does justice to all three.

The Val d'Orcia is at its most beautiful in April and October — in April, when the wheat is luminously green and the almond orchards are flowering along the ridges, and in October, when the stubble fields turn amber and the light comes in at a low angle that turns every cypress shadow into a line of dark gold.

This is the UNESCO landscape of cypress-flanked roads and isolated farmhouses and hilltop towns that has provided the backdrop for a significant proportion of the world's Tuscan fantasy, and it is not diminished by familiarity. It is genuinely as beautiful as it appears in every photograph, and the wines and the food produced within its boundaries are genuinely as good as they are claimed to be. We have spent years designing programmes in this territory, and the combination of Montalcino's Brunello, Montepulciano's Vino Nobile and Pienza's Pecorino — with the cypress avenues and the thermal springs and the sunsets over Monte Amiata in between — remains one of the itineraries we are most proud to offer.

The best approach to the Val d'Orcia wine programme is not to rush between producers but to spend two full days — one centred on Montalcino, one on Montepulciano — moving between cellar visits at a pace that allows for unhurried conversation with the winemakers and for the tasting notes to settle before the next flight is poured. We supplement the programme with a morning in Pienza (thirty minutes between the two wine towns) and a late-afternoon drive through the Val d'Orcia landscape itself — the strade bianche, the gravel roads between the cypress avenues — which is best experienced from a private car with no schedule and no destination, at the hour when the shadows are longest.

Montalcino: Brunello and the Long Game

Brunello di Montalcino DOCG — produced exclusively from Sangiovese Grosso on the hillsides surrounding the fortress town of Montalcino, aged for a minimum of four years before release, with up to two years in large Slavonian oak and a further period in bottle — is one of the most sought-after, most discussed and most misunderstood red wines in Italy. Great Brunello from great vintages requires ten, fifteen or twenty years of cellaring to arrive at the condition in which its full complexity — dried rose, tar, mineral earth, the iron-and-chalk character of the Montalcino soils — fully unfolds.

We visit producers across the full range of the zone: the great historic estates whose wines defined the category, and the small biodynamic producers of the outer zones whose access to their cellars is available only through personal introduction. Vertical tastings of twelve to twenty vintages, conducted by the winemakers, are available by arrangement and are among the most complete wine experiences we design.

Montepulciano: Vino Nobile and the Perfect Hilltop

The Vino Nobile di Montepulciano DOCG — Sangiovese here called Prugnolo Gentile, grown on volcanic clay soils and aged for a minimum of two years — is the most approachable of the great Tuscan Sangiovese wines and, in the finest expressions, one of the most elegant. The town of Montepulciano is itself among the most perfectly preserved Renaissance hilltop cities in Tuscany: a single long corso rising steeply between Renaissance palaces by Sangallo and Vignola to the Piazza Grande and the unfinished Duomo, with views over two valleys in opposite directions from every high point. The Cantina Contucci, whose vaulted cellars run beneath the Palazzo Contucci in the main square and in which wine has been produced continuously for more than five hundred years, is one of the most atmospherically compelling winery visits in Italy.

Pienza: The City That Was an Idea

Pienza was built in the 1460s as a physical expression of a philosophical proposition: that a city, designed by a humanist architect to humanist principles, could be beautiful in the way that an argument can be beautiful — coherent, well-proportioned, complete. Pope Pius II commissioned Bernardo Rossellino to rebuild his natal village of Corsignano on a single trapezoidal piazza, and the result — the cathedral, the papal palace, the bishop's palace and the town hall arranged in a composition unchanged in five hundred and fifty years — is one of the most exact surviving expressions of the Renaissance ideal of the city as a work of art. The Pecorino di Pienza, aged in local cave-cellars and ranging from fresh and creamy to intensely savoury after two years of stagionatura, is tasted in the small shops of the main street alongside the local honey and fig preserves that are its natural companions. The combination of architectural perfection and excellent cheese is, in its quiet way, very Tuscany.

A private vertical tasting of Brunello di Montalcino across fifteen consecutive vintages — in the cellar, at the estate, with the winemaker who made each wine — is one of the three or four most complete wine experiences we have ever designed for a client.

The Essentials

Best season: April and October for the Val d'Orcia landscape; year-round for Brunello and Vino Nobile

Signature experience: Brunello vertical tasting (12–20 vintages) at a historic Montalcino estate; Bagno Vignoni thermal pool

Stay: Converted farmhouses in the Val d'Orcia, Castiglione d'Orcia, or Montepulciano

Combine with: Siena (one hour north), Chianti Classico (two hours north), Bolgheri (one hour west)

Every journey we design is entirely bespoke — crafted around your preferences,your pace, and your desire for the exceptional.

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