Cycle Through Siena & Chianti

Day 1
Trip starts at our hotel in San Quirico. After the trip briefing, hired bikes are issued to clients. The leader will arrange an optional group meal, normally taken at the hotel's own restaurant.

Day 2
Following an ancient pilgrimage route, the Via Francigena, we head towards Pienza, a charming town full of history and culture. From here we cycle to the wine centre of Montepulciano, famous for its Vino Nobile. We then head towards the mediaeval village of Monticchiello and on to Bagno Vignoni, before making our way back to the hotel.
Distance cycled 61km

Day 3
A classic day's riding, showing Tuscany at its most picturesque. Following quiet roads we head out of San Quirico with a first stop at Montalcino. We then descend on gravel roads via Castiglione del Bosco and the road to Murlo. 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 town of Siena.
Distance cycled 60km

Day 4
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 and the Campo, Siena's wonderful main square. Alternatively you may choose to head out for an unguided ride.

Day 5
From Siena we head directly into the heart of Chianti. Our route takes us via some lovely small villages and hamlets, as well as some spectacular vineyards and castles, such as that of Castello di Brolio. Here there is the option to take a wine tasting of the some of the area's finest wines. We then cycle via Gaiole and Radda in Chianti, with options to ride to the abbey of Coltribuono, before our final section to Castellina in Chianti, where we stay for two nights.
Distance cycled 55km

Day 6
From Castellina, we travel through some lovely countryside before taking an amazingly scenic descent into the lower valley. From Poggibonsi we head towards the distant towers of San Gimignano nestling between the hills and small hamlets. San Gimignano is sometimes crowded, but this does not take away from what is one of the most interesting sights in Tuscany. We spend a few hours enjoying the atmosphere, walking by the walls and admiring the town's high towers. Our return route passes through the quieter Colle di Val d'Elsa, and on to the walled town Monteriggioni, before returning to Chianti and the quiet roads leading to our lodge. There is an option to take a transfer back to Castellina from Monteriggioni.
Distance cycled 56km

Day 7
From our hotel in Castellina, we first ride to a spectacular panoramic road via San Donato in Poggio towards Panzano in Chianti, before taking a back road via lovely walled village of Montefioralle and then to Greve in Chianti. Here we have time for lunch and to admire the market square, before heading towards Stada and Impruneta, home to terracotta production. We finally take a panoramic road towards Florence, cycling all the way to Piazzale Michelangelo for a final group shot. We will arrive in Florence in the eaaly afternoon, which will give you time to start to explore this beautiful city.
Distance cycled 62km

Day 8
The trip finished in Florence after breakfast. Please speak to our sales team if you would like to book extra nights in Florence.