We leave from the Val d’Elsa, which is dominated by the towers of San Gimignano and the nearby city of Volterra. The road that leads to Poggibonsi and Colle Val d’Elsa snake up to the hills that face west, overlooking the towns of Casole d’Elsa, Mensano, Monteguidi and Radicondoli. These are true treasures of the Siena territory, vaunting an excellent position between the Tyrrhenian Sea and the coastal Maremma area.
In Pievescola, you’ll be immersed in the intimate and silent atmosphere of the Montagnola hills; from continue on to the wilder and lesser-known Val di Merse, the perfect place for to discover the mysteries and charms of the ancient Etruscan people in the area near Murlo. And once you’re in Murlo, take a moment to admire the stunning roof-less basilica of San Galgano: trust us, you won’t regret it!
From Buonconvento, you can dive right into the Crete Sienese and ride along the historic pilgrimage route via Francigena, before it overlaps with the via Cassia. After crossing the Ombrone River, the itinerary continues up into the hills and vineyards, where the area's world-famous Brunello wine is made, in Montalcino, a fantastic vista point overlooking the Val d’Orcia. Surrounded by vineyards, the journey moves to Castelnuovo dell’Abate, where you can discover the mystic silence of the Abbey of Sant'Antimo.
Cyclists are now in the southern part of the Siena province, as the route travels up towards Monte Amiata, an ancient volcano, now dormant, covered in chestnut and beechnut trees. All around the area, you’ll find an authentic Tuscany, one that refuses to appear like any other places and which links its identity with the volcano and the intimacy of its forests.
Monte Amiata, which borders the provinces of Siena and Grosseto, is a great place to admire the blue of the sea and the sky. The Ombrone and Orcia rivers meet at the base of the mountain before winding into the Maremma.
From here, head towards the fortress in Radicofani, where the harmonious landscape dominates the surrounding countryside, part of the stunning Val d’Orcia Artistic, Natural and Cultural Park.
The journey moves north, crossing the entire valley before reaching Pienza, an excellent example of a purely Renaissance city and a must-see. The next stop is Montepulciano, home to many cellars and winemakers producing Vino Nobile. The magic of the surrounding landscape is, indeed, considered 'artistic' – thanks to the harmonious design of a territory that’s been created by both nature and man. The landscape becomes all the more remarkable as cyclists approach San Giovanni d’Asso, Trequanda and Asciano.
The last part of the journey takes place in the silent and beautiful Chianti area, among vineyards, villas and castles, where the presence of man is more or less unnoticeable and the roads have been saved from the sounds and vibrations of large cars. Here, the Siena skyline seems to fade away in the sunset, and the last stops to take are in the stunning Chianti towns of Castelnuovo Berardenga, Gaiole, Radda and Castellina. The last 18-km stretch will take you back to Poggibonsi.