History and Wine in Val D'Orcia: Pienza & Montepulciano with Visit and Lunch at Cantina Talosa

Explore the Renaissance charm of Pienza, indulge in organic farm-to-table dining, and savor the architectural beauty and renowned wines of Montepulciano

From Siena, head south into the Val d'Orcia for a day combining two of its finest hill towns with an extraordinary underground wine and lunch experience in Montepulciano. Your first stop is Pienza, the UNESCO-listed Renaissance village conceived by Pope Pius II. Explore Piazza Pio II at your own pace, visit the cathedral with its luminous interior and browse the local shops for the region's celebrated pecorino cheese before continuing south.

In Montepulciano, you'll descend into the Historical Cellar of Cantina Talosa, accessed via a 15-metre staircase from the wine shop on Via Talosa. The 16th-century vaulted tunnels lead past ancient barrels to an authentic Etruscan tomb dating from the 5th century BC. A guided tasting of four wines follows — including Vino Nobile di Montepulciano Riserva and the Filai Lunghi cru — paired with bruschetta with estate olive oil, Pienza pecorino and Tuscan cold cuts.

After the cellar experience, free time to explore Montepulciano's sloping streets and Renaissance architecture before returning to Siena.