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A biking tour of the Sienese countryside

An inspiring and evocative itinerary

The Giro Terre di Siena route is a ring that winds around the Siena province, travelling through: Val d'Elsa, Val di Merse, Val d'Orcia, Amiata, Val d'Orcia again, Crete Senesi and the Chianti. The itinerary does not travel into Siena, but it can be easily reached by way of several connecting roads, located in the following areas: Castellina in Chianti (21 km), Poggibonsi (26 km), Rosia (16 km) and Asciano (26 km).
From the Torre del Mangia in Siena, which dominated the city's rooftops and the Campo square below it, one has a 360 degree view of the surrounding countryside, woods, fields and small hamlets. In actual fact, the Terre di Siena are comprised of a variety of areas, each one characterized by its own unique identity.
Departing from the north, in a counter-clockwise direction, the Giro delle Terre di Siena travels through the many different areas that make up this remarkable province. 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 go up in the hills that face west, overlooking the towns of Casole d’Elsa, Mensano, Monteguidi and Radicondoli. These are true treasures of the Terre di Siena territory, in proximity to the Tyrrhenian Sea and the coastal Maremma area.
In Pievescola, cyclists are immersed in the intimate and silent atmosphere of Montagnola; from here they continue on to the wilder and lesser known Val di Merse, the perfect place for cycling pioneers that want to discover the mysteries and charms of the ancient Etruscan people, in an area near Murlo. From Murlo, cyclists can admire the stunning roof-less basilica of San Galgano.
In Buonconvento, cyclists enter the Crete Sienese area, and ride across the ancient Via Francigena, which coincides here with the Via Cassia. After passing over the Ombrone river, the itinerary conitnues up into the hills and vineyards of the area's world-famous Brunello wine to reach Montalcino, a fantastic panoramic point overlooking the Val d’Orcia. Among the vineyards, the itinerary continues to Castelnuovo dell’Abate to discover the mystic silence of the Sant'Antimo Abbey. Cyclists are now in the southern part of the Siena province, and the route travels up towards Monte Amiata, an ancient volcano, now dormant, that is covered in chestnut and beechnut trees.
Monte Amiata, which borders on the provinces of Siena and Grosseto, is a great place to admire the blue of the sea and the sky. At the base of the mountain, the Ombrone and Orcia rivers meet, and lead to the Maremma. From here, cyclists continue on to the Rocca di Radicofani, where the harmonious landscape dominates the surrounding countryside, which also comprises the Artistic and Cultural Natural Park.
The journey continues north, and the route crosses all of the Val d'Orcia reaching Pienza, an excellent example of a Renaissance city and a must along the journey. The next stop is Montepulciano, home to many cellars and winemakers that produce Vino Nobile. The magic of the surrounding landscape is, indeed, considered 'artistic' – thanks to the harmonious design of a territory that has been created by both nature and man. The landscape becomes all the more remarkable as cyclists approach San Giovanni d’Asso a Trequanda and Asciano.
The last part of the journey takes place in the silent and beautiful Chianti area, among vineyards, villas and acstles, where the presence of man is more or less unnoticeable and the roads have been saved from the sounds and vibrations of marge motors. 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 takes cyclists back to Poggibonsi.
Point of departure and arrival: Poggibonsi
Distance: 395 km
Total climb: 7,010 metres
Type of road: mostly asphalt
Type of bike: hybrid, road
Difficulty: challenging