Day 1  :  Gaiole in Chianti  -  Siena  -  41 km.  -  From the heart of Chianti Classico we'll be cycling towards Siena, visiting the XIIth century castles of Meleto and Cacchiano, (both partially  turned into villas during the XVIIIth century), and enjoying great views over Orcia Valley and Monte Amiata, (a 1770 m. extinct volcano).

Day 2  :  Siena  -  Buonconvento  -  40 km.  -  Cycling across the Crete Senesi we'll be passing the scenic medieval village of Radi and the XII century hamlet of Murlo before reaching Buonconvento, a fortified town on the Via Francigena which is also classified as one of the most beautiful ancient Italian towns.

Day 3  :  Buonconvento  -  San Quirico D'Orcia  -  46 km.  -  A long and steep uphill on dirt road will lead us to the scenic medieval village of montalcino, worlwide famous for the production of one of the best Tuscan wines, the Brunello. From there, cycling mainly downhill across an endless sea of vineyards, we'll reach the fortified village of San Quirico D'Orcia, one of the ancient gateways of Orcia Valley.

Day 4  :  San Quirico d'Orcia  -  San Quirico D'Orcia  -  50 km.  -  During the 4th day we'll follow a sort of ring-shaped itinerary through the scenic Val D'Orcia visiting the tiny medieval village of Bagno Vignoni, built around a thermal water pool, and the Renaissance town of Pienza.

Day 5  :  San Quirico d'Orcia  -  Buonconvento  -  50 km.  -  The fifth leg is a very suggestive ride across the typical clay landscape of the so-called Crete Senesi. During this leg we'll take our time to visit the Abbey of Monte Oliveto Maggiore, built in the XIVth century by the Olivetan monks.

Day 6  :  Buonconvento  -  Castelnuovo Berardenga  -  37 km.  -  Today we'll be biking towards the southernmost part of Chianti, reaching the ancient town of Castelnuovo Berardenga, founded by the Republic of Siena in the XIVth century.