Between Bibbiano and Montalcino lies one of the most challenging sections of the route. You’ll cross the beautiful and panoramic hills where the Sangiovese grapes are grown, the crown jewel of Brunello di Montalcino production. This stretch features one of the toughest gravel roads: the climb of Castiglion del Bosco, made famous by the legendary stage of the 2010 Giro d’Italia. Once the climb is over, cyclists can enjoy one of the most stunning views at the entrance to the cypress-lined avenue of the Corte Pavone winery, a perfect stop before reaching the home of Brunello: Montalcino, along the old Via Francigena. Montalcino is world-renowned for its ancient history and architectural beauty, including the 13th-century Palazzo del Priore with its heraldic crests and towering medieval spire, the symbol of this magnificent town. A visit to the pentagonal fortress built in 1361 at the highest point of the city is a must, where international events are often held!

Points of interest: S. Antonio Chapel (Bibbiano), S. Michele Church (Castiglion del Bosco), Montalcino Fortress, Church of Sant’Agostino.