The Tuscan landscape is one of the most evocative and romantic in Europe with cypress trees lining the roads, olive groves, vineyards, ancient hill-top towns and classic Renaissance cities. This group cycling tour is carefully planned to take in the best of Tuscany without feeling rushed: part of the joy of the Italian lifestyle is watching the world go by with a glass of Chianti in your hand!

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Why We Love It

You can ride along the quiet roads of classic Tuscany and visit some of this scenic region’s best towns and villages

Enjoy famous Tuscan cuisine and wine while cycling to wine centres and through vineyards for leisurely lunches

Relax in the beautiful city of Florence and explore this Renaissance city at your leisure with a free afternoon

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Day by day Itinerary

Cycle Siena & Chianti

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Day 1

San Quirico

Start San Quirico, in the heart of Val d'Orcia. 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

San Quirico

Following an ancient pilgrimage route, the Via Francigena, head towards Pienza, a charming town full of history and culture. From here cycle to the wine centre of Montepulciano, famous for its Vino Nobile. Head towards the medieval village of Monticchiello and on to Bagno Vignoni, before making your way back to the hotel.

Day 3

San Quirico - Siena

A classic day's riding, showing Tuscany at its most picturesque. Following quiet roads, head out of San Quirico with a first stop at Montalcino. Then descend on gravel roads via Castiglione del Bosco and the road to Murlo. From here ascend the short but steep Rospatoio Pass and take a lovely road section via Ville di Corsano, as you approach the splendid Gothic town of Siena.

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

Siena - Castellina

From Siena head directly into the heart of Chianti. Your route takes you 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. Then cycle via Gaiole and Radda in Chianti, with options to ride to the abbey of Coltribuono, before your final section to Castellina in Chianti, where you stay for two nights.

Day 6


From Castellina, travel through some lovely countryside before taking an amazingly scenic descent into the lower valley. From Poggibonsi 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. Spend a few hours enjoying the atmosphere, walking by the walls and admiring the town's high towers. Your 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.

Day 7

Castellina - Florence

From your hotel in Castellina, 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 you have time for lunch and to admire the market square, before heading towards Stada and Impruneta, home to terracotta production. Finally, take a panoramic road towards Florence, cycling all the way to Piazzale Michelangelo for a final group shot. You will arrive in Florence in the early afternoon, which will give you time to start to explore this beautiful city.

Day 8


Your tour ends this morning in Florence.

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