Leaving Trequanda in the direction of Montisi is easy to find, after two kilometers, the junction that leads to the farm of Colle, where the remains of a hermitage that Leopold of Habsburg used as a refuge for secret love meetings are visible in the oldest part of the villa.

Back on the main street you will find Montelifrè, an ancient village born from a Roman castrum and transformed in the Middle Ages in an imposing castle which became a long time feud of the Cacciaconti family.

A romantic wood of holm oaks, which turns red at the time of the cyclamens, still hides secrets like the old mills and the ruins of the castle.
Once at the gates of Montisi, take the beautiful dirt road on the left that, after reaching the highest point at 567 meters, with a further detour, leads to Villa Salimbeni. Those who have the curiosity can go in search of the mysterious Etruscan settlement.

Continuing on, one easily reaches Petroio, a picturesque medieval village and a major center for the craftsmanship of terracotta.

In Petroio was born Bartolomeo Carosi, a.k.a. Brandano, the madman of Christ. Brandano, interrupted his youth of blasphemer electrocuted by faith and began to wander, dressed in a white tunic, barefoot and with a skull and a crucifix in his hand. His invectives against the powerful were accompanied by prophecies and misfortunes. Even today in a wooded limestone plateau you can visit his home, a cave known as the «Buca del Romito». A terracotta statue placed in the historical center of the village remembers Brandano.

A beautiful panoramic road leads to the nearby village of Castelmuzio, of Etruscan-Roman origins. First domain of the Cacciaconti and then of the Salimbeni, it was purchased by the Piccolomini, who remained there until the conquest of Siena, and then passed to the Grand Duchy of Tuscany. Unlike Petroio, Castelmuzio was one of the places preferred by San Bernardino to hold his famous sermons. In Castelmuzio, the Spedale di San Giovanni Battista contained a pharmacy and a hospice for pilgrims traveling along the Via Francigena. Today the historical route does not provide, unfortunately, the passage from Castelmuzio but very close passes the ancient Lauretana.

To reach Montisi you have to go down to the Rigo torrent and then face a nice stretch among secular olive trees. Montisi has Etruscan origins so much so that its name comes from «Monte» and «Iside», the Etruscan goddess to whom a temple was dedicated, standing on the site of the current Pieve di Santo Stefano a Cennano. The parish church of Santissima Annunziata is the main place of worship of the town where, after the troubled medieval period, followed the centuries of poverty alleviated with the cultivation of saffron. Only in the last centuries the flourishing production activity of the precious olive oil has started.

From Montisi, the road becomes wider and smoother until it rejoins the outward journey and reaches Trequanda dominated by the Cacciaconti castle with the beautiful Romanesque church of Saints Peter and Andrew.

One tip: use the superfine local oil to season every dish you are offered.