Tuscany: Cycle Siena & Chianti

We start in the Orcia Valley, staying in one the local hilltop towns, San Quirico D'Orcia or Pienza. There’ll be a welcome briefing at the hotel, where we gather as a group to go over the trip ahead.

Today we enjoy a circular ride in the Orcia Valley. Taking in Pienza and San Quirico d'Orcia, we cycle to the beautifully situated wine centre of Montepulciano, best known for producing vino nobile. We then head towards the medieval village of Monticchiello and on to the well known thermal bath of Bagno Vignoni, before making our way back to the hotel.

A classic day's riding, showing Tuscany at its most picturesque. Following back roads, we head out of San Quirico with a first stop at Montalcino. We then descend on the road to Buonconvento and ride back up to Murlo, passing by Bibbiano. From here, we ascend the short but steep Rospatoio Pass and take a lovely road section via Ville di Corsano as we approach the splendid gothic city of Siena.



If staying in Pienza (26 August 2023 departure), today's ride is an extra 6mi (10km).

Siena is one of the best-preserved medieval towns in Italy and home to the grand Piazza del Campo. There is plenty to see in Siena and its sights are best explored on foot as the town is compact but hilly. There are many museums and buildings of interest to visit, such as the impressive duomo (cathedral). Alternatively, you may choose to head out for an unguided ride.

From Siena, we head directly into the heart of Chianti. Our picturesque route takes us via some lovely small villages and hamlets, plus spectacular vineyards and castles, such as Castello di Brolio. Here there is the option to taste some of the finest regional wines. We then cycle on to Gaiole for lunch and, after a gelato stop in Radda, follow our final section to Castellina in Chianti, where we stay for two nights.

From Castellina, we ride through rolling countryside before taking a scenic descent into the lower valley. From Poggibonsi, we head towards the distant towers of San Gimignano, nestled between hills and small hamlets. The Unesco-recognised town, famous for its towers, vernaccia wine and saffron, is one of the most visited and interesting sights in Tuscany. We spend a few hours enjoying the atmosphere, walking by the walls and admiring the high towers. Our return involves a long but beautiful climb before reaching Castellina and a well-deserved gelato.

Our final ride passes through Panzano towards the market town of Greve in Chianti. This is considered one of the most scenic roads in Tuscany, which links Florence to Siena via the Chianti hills. On arrival in Greve in Chianti, we have time to admire the triangular piazza that hosts the Chianti wine festival before heading towards Strada and Impruneta, known for their terracotta production. In Impruneta, we stop for lunch. We finish by taking a panoramic road towards Florence, cycling all the way to Piazzale Michelangelo. We will arrive in Florence in the early afternoon, giving you time to start exploring this wonderful Renaissance city, including the cathedral and Baptistery of Saint John. Don’t miss the Ponte Vecchio, a medieval stone bridge lined with jewellers, which connects the two banks of the river Arno.

The trip comes to an end after breakfast. However, if you’d like a little longer to explore this magnificent city, please speak to your sales representative.