Southeast of Siena, not far from the border of the Tuscan Maremma, the towns of Montepulciano, Montalcino, and Pienza are Tuscan classics. Perched on a ridge 600 meters above sea level and enclosed by fortified walls, Montepulciano still shows the original characteristics of a typical medieval urban center.
The Piazza Grande is built on the highest point of the ridge.
Start in Montepulciano’s Piazza Grande and take the panoramic path to Porta dei Grassi, where you will encounter the Tempio di San Biagio. Then take the Via dei Canneti until you reach the intersection with Via delle Colombelle.
The path follows the mountain ridge and leads you through the Nobile vineyards to the oratory of Sant'Anna in Via dei Colli, in the foothills of Montefollonico. Stop in Montefollonico for lunch.
This track also passes the magic picnic spot of Il Tondo, east of Montefollonico, a secret garden created in the 19th century. You can discover Il Tondo and walk around the hill, or you can skip this option.
From Il Tondo walk down following Via dei Frati towards Montefollonico (you walk around Residence Sangismondo), then left on Via dei Frati and again left on Via dei Giglio. On Via dei Pianelli you can enter the old center of Montefollonico climbing the stairs in front of you, or walk towards Bar Sport (to the right).
Bar Sport on Via Pianelli is a good spot for a coffee or a refreshing drink. Here the locals watch tourists passing by. In front of Bar Sport, you can enter the historical medieval center of Montefollonico through Porta del Pianello. A lunch in one of the two excellent restaurants in Montefollonico is recommended.
Approximate distance: 19 km
Time: 3,5 - 4 hours
Total climb 401 m | Total descent 486 m