TUSCANY'S WINE TOWNS
Montepulciano & Montalcino: Tuscany's Wine Hill Towns
Two hilltop wine towns south of Siena, their prized reds Vino Nobile and Brunello, and the UNESCO-listed Val d'Orcia countryside that surrounds them both.
See Tuscany day trips on GetYourGuide ↗Montepulciano, Montalcino & San Gimignano wines, compared
| Wine | Town | Style |
|---|---|---|
| Vino Nobile di Montepulciano | Montepulciano | Sangiovese-based red, DOCG, generally softer and more approachable young |
| Brunello di Montalcino | Montalcino | Sangiovese Grosso red, DOCG, structured and built for extended ageing |
| Vernaccia di San Gimignano | San Gimignano | Crisp mineral white, Italy's first-ever DOC (1966), later DOCG |
Montepulciano and Vino Nobile
Montepulciano is a long, narrow hill town strung along a ridge in southern Tuscany, its main street (the Corso) climbing steeply between Renaissance palazzi to the hilltop Piazza Grande. Beneath the town runs a network of ancient cellars, many open for tastings, producing Vino Nobile di Montepulciano — a Sangiovese-based red that was among the first Italian wines to receive DOCG status, the country's highest wine classification. The town itself is worth the climb on its own merits: it's a showcase of Renaissance architecture, largely reshaped by architects working for the Medici and other patrons in the 15th and 16th centuries.
A film stand-in for Volterra
Montepulciano has one unusual claim to modern fame: for the 2009 film The Twilight Saga: New Moon, the production filmed its scenes set in Volterra — the fictional vampire coven's city — largely in Montepulciano instead, using its Piazza Grande and surrounding streets as the backdrop. Fans occasionally visit hoping to retrace those scenes, which can cause some confusion with the real Volterra, a separate hill town roughly an hour away with its own distinct Etruscan history and no connection to the film shoot beyond lending its name to the story.
Montalcino and Brunello
A short drive from Montepulciano, Montalcino is smaller and quieter, dominated by its 14th-century Fortezza (fortress), whose ramparts give sweeping views over vineyards in every direction. It's the home of Brunello di Montalcino, one of Italy's most celebrated reds, made from a specific Sangiovese clone (Sangiovese Grosso) grown almost exclusively on the hills around the town. Brunello carries strict production rules, including extended ageing before release, which contributes to its reputation and its price. Enotecas around the central piazza and inside the Fortezza itself offer tastings for visitors who'd rather sample a glass than commit to a full cellar visit.
The Val d'Orcia landscape between them
Montepulciano and Montalcino both sit within the Val d'Orcia, a valley of rolling clay hills, cypress-lined roads, and scattered farmhouses recognised by UNESCO as a World Heritage cultural landscape in 2004 — protected not for a single monument but for an entire agrarian countryside shaped over centuries into what became the archetypal image of rural Tuscany. The valley's honey-coloured hills and famously photogenic winding roads (several near the village of San Quirico d'Orcia) are widely reproduced in Tuscan tourism imagery, and driving between the wine towns here is as much the point of a visit as any single stop.
Choosing between them
If time only allows one wine town, the choice comes down to taste: Montepulciano offers grander Renaissance architecture, a livelier main street, and Vino Nobile's slightly softer style, while Montalcino is smaller and more purely wine-focused, with Brunello's bigger reputation and a fortress setting that rewards a slow wander. Many visitors based in Siena or Florence combine both towns with the Val d'Orcia's back roads into a single day given the driving distances involved, rather than treating either as a full day trip on its own — worth checking against a specific tour's itinerary before booking.