From Siena: Pienza and Montepulciano Small-Group Tour｜Italy

Travel along one of the most panoramic roads in Tuscany, driving the characteristic moonscape of the Crete Senesi en route to the medieval hamlet of Pienza in the Val d’Orcia valley.

One of the first towns to be entirely planned on paper by important architects and artists of the time, Pienza was commissioned by Pope Pius II - the humanist pope - to help him renovate his native town and bring it to new splendor. A wholesome lunch, based on fresh local ingredients will be waiting on a beautiful terrace (weather permitting) at a local farm.

Continue in the afternoon to Montepulciano, one of Tuscany’s largest hill towns. Under the dominance of Siena in the Middle Ages, and Florence during the Renaissance, today it is renowned for its wine. See influences from both towns in the architecture and art of the historic center, located on a steep hill with beautiful views of the Tuscan and Umbrian border.

Go to the main Piazza Grande, tour one of the many wineries carved out of the earth below the city and discover some of the palaces of the noble families that once lived here. Taste the Vino Nobile local wine and continue to explore the palaces, churches and streets on your own. As you follow the route of the main road downhill, imagine how hard the “Bravio delle Botti” festival must be; a competition to race wine barrels from the bottom to the top of the hill!