History and Brunello Wine - Prestige: Pienza & Montalcino with Visit and Lunch at Tenuta di Argiano

Savor Brunello wine and explore the Renaissance towns of Pienza and Montalcino

From Cortona, travel south into the UNESCO-listed Val d'Orcia for a day that moves between two of Tuscany's most iconic medieval towns and one of Brunello's founding estates. Your first stop is Montalcino, a hilltop fortress town with sweeping views over three valleys. Spend an hour at your own pace — wander the medieval streets, step up to the 14th-century fortress ramparts and browse the enotecas that line the main street.

From Montalcino, a short drive brings you to Argiano, a 16th-century Renaissance villa set among Sangiovese vineyards at Sant'Angelo in Colle. Over 2.5 hours you'll walk through the vineyard and formal gardens, descend into the historic cellars and visit the private rooms of the Villa — home to ongoing restoration work and Renaissance art. A 4-course seasonal lunch follows, paired with five estate wines including Argiano's Brunello di Montalcino, presented by the estate sommelier.

The afternoon takes you to Pienza, the ideal Renaissance city commissioned by Pope Pius II. Stroll Piazza Pio II, admire the luminous interior of the cathedral and take in the iconic Val d'Orcia panorama from the town walls before returning to Cortona.