Montepulciano

A Renaissance hilltop town perched above vineyards producing the celebrated Vino Nobile wine. Its steep stone streets lead to elegant palazzi and a spectacular main piazza.

Things to do

• Wine tasting in the cellars — Many enotecas along Via Gracciano offer free tastings of Vino Nobile directly from the barrel.
• Visit Piazza Grande — The hilltop main square features the Palazzo Comunale with a tower offering sweeping valley views.
• See Tempio di San Biagio — A stunning Renaissance church sitting alone in the fields below town, best visited at golden hour.
• Walk the medieval walls — Circumnavigate the hilltop along the old walls for dramatic views over Val d'Orcia and Val di Chiana.
• Attend the Bravio delle Botti — In August, barrel-rolling teams race uphill through town in a colourful medieval tradition.

Food to try

• Vino Nobile di Montepulciano — A robust DOCG red wine made from Sangiovese grapes aged in oak barrels.
• Pici all'Aglione — Thick hand-rolled pasta served in a bold garlic and tomato sauce typical of the area.
• Pecorino di Pienza — A nearby sheep's milk cheese ranging from fresh and mild to aged and sharp.
• Cantucci con Vin Santo — Almond biscotti dipped in sweet fortified Vin Santo wine, a classic Tuscan dessert ritual.

Local customs & good to know

• Wear comfortable shoes — The streets are steep and cobbled; flat-soled sturdy footwear is essential.
• Buy wine directly from producers — Purchasing from local cantinas supports small estates and often gets you better prices.
• Arrive early or late in summer — Midday heat in July and August can be intense; mornings and evenings are far more pleasant.