Montepulciano sits on a ridge between the Val di Chiana and the Val d'Orcia, a Renaissance town of such beauty that it was used as the stand-in for Volterra in the Twilight films (Volterra itself was apparently not photogenic enough). But Montepulciano's real claim is its wine: Vino Nobile di Montepulciano DOCG, made from Prugnolo Gentile (Sangiovese Grosso), aged for a minimum of 2 years (3 for Riserva), was the first Italian wine to receive DOCG status in 1980. The cellars are dug into the tufa beneath the town — some stretch under piazzas and churches, reaching temperatures and humidity levels that have been aging wine since the 15th century. Tasting rooms open directly onto medieval streets. You walk out of a cellar into a piazza designed by Antonio da Sangallo, holding a glass of wine the Medici drank. Tuscany guide → · Val d'Orcia →
Plan my Tuscany wine trip →Avignonesi: One of the historic estates — biodynamic since 2009, the Vin Santo aged in small barrels for 10 years is legendary. Beautiful property. €20-35 tasting. Boscarelli: Family-owned since the 1960s, consistently producing the most elegant Vino Nobile. The Nocio dei Boscarelli single-vineyard is extraordinary. €15-25. Poliziano: Federico Carletti's modern-styled wines from the Asinone cru — powerful, intense. €15-30. Contucci: The oldest cantina in Montepulciano — cellars beneath Palazzo Contucci on the Piazza Grande. The entrance is literally on the main piazza. Free tasting at the counter. De' Ricci: Cellars under the town, accessible by a spiral staircase from street level. Tours of the underground network. €15-20.
Getting there: Montepulciano is between Siena and Perugia. Nearest station: Chiusi-Chianciano Terme (Trenitalia Rome-Florence line, 1.5h from Rome, 2h from Florence), then bus (30min) or car (20min). By car: 1.5h from Florence, 1h from Siena. Stay: Montepulciano centro storico (€70-140/night — stay inside the walls), or agriturismi in the surrounding countryside (€60-120). Eat: Osteria Acquacheta (famous for its bistecca alla fiorentina, €30-45), La Grotta (elegant, facing the Tempio di San Biagio, €40-55). Wine prices retail: Vino Nobile €12-25, Riserva €20-45. Combine with: Pienza (15min — pecorino cheese capital), Montalcino (30min — Brunello), Val d'Orcia (Montepulciano IS the eastern gate).