Tuscany road bike tour from Florence to Siena

An 8 day tour through the Chianti
Cycling tour
Cycling Tours
Difficulty level 4
Individual tour
Self guided tour
code: ITTOS03C


from 980€

Chianti road bike tour: emotion, scents and traditions

Florence-Mugello-Chianti-Siena-San Gimignano-Montalcino

This is a lovely road bike adventure through one of the most famous Italian regions, Tuscany. This stunning land is famous for its wines, its cities rich in art, and the warm welcome you get from its inhabitants: a winning combination of emotions, scents, and traditions perfectly combined and ready to be discovered by bike. It is a tour that unites two of the most famous squares in Italy: Piazza della Signoria in FLORENCE and Piazza del Campo in Siena. After a Grand Fondo round tour in the surroundings of Florence, the amazing town of Leonardo, Giotto, Dante and Brunelleschi, you leave it to cross the Chianti area and enjoy the hills, its varied and coloured landscapes.

Cycling along the “road of wines” of the famous Chianti, you will have the possibility to taste wine in the numerous local wine cellars. Discover the dirt roads of the famous Eroica, a yearly returning event for vintage road bikes, and take the time to visit picturesque towns like Radda in Chianti, Gaiole, and Castellina in Chianti. For the next few days, you will stay in another wonderful art town, Siena famous for the Palio. With some loop rides, you will discover the hilly surroundings of the town emerging yourself into the heart of Tuscany. A nice ride brings you to San Gimignano, the town of many towers and another route dives into another divine wine-area with a characteristic wine town, Montalcino. Taste the wines in one of the many wine bars and small restaurants combined with a nice pici- pasta, local pecorino-cheese, a Fiorentina steak, or a delicious bean soup. All in all, a perfect recipe for an unforgettable holiday in Italy.


The daily program of the 7-day tour

Magical and charming Florence, there are not enough words to describe this art town. There is so overwhelming much to see, that you should take some extra days to savor the city in all its aspects, to walk around and feel its heart beating, see all the worldwide famous monuments, museums or just enjoy sitting on a terrace drinking a cappuccino, a fresh beer or Chianti wine watching all the people passing by and be happy you are in this one of a kind town.


Overnight stay with breakfast in Florence.

Florence is surrounded by a lush country side inviting you to make a nice ride to explore it. Today’s stage is an average route of the Florence GranFondo and crosses a beautiful rolling hilly landscape dotted with villas and farmhouses. There are two climbs over 800m and two others of about 400m. The Mugello area is a wide green valley with a varied landscape, surrounded by hills and crossed by the river Sieve. To make a break there is the cosy town of Scarperia, once founded by the Florentine Republic as a defence post for the town of Florence.


Overnight stay with breakfast in Florence

Distance 113 km / 70 miles

Ascent/descent: + 2300m -2300m

It will not be easy to leave Florence, but another stunning area awaits us… the hilly landscape of the Chianti characterized by hills covered with woods alternated by immense vineyards of this famous vine area. On some stretches, hills will change into a more challenging landscape with lower mountains. In Chianti, there are lovely and fascinating small towns like Panzano, Radda in Chianti and Gaiole. In Gaiole starts the route of the Eroica, a yearly cycling event with vintage racing bikes. It recalls an ancient way of road bike cycling, more pure, and immersed into nature and enjoying it in full relax. This route follows the famous well paved dirt roads, characteristic of this region. You will cross the Chianti Classico area and it goes up to Castello di Brolio, a jewel of the Ricasoli family with splendid views and excellent wines. Then freewheeling downhill through vineyards towards Siena, which appears on the horizon as in a postcard. Siena is masterpiece of art, with the famous cathedral that houses the Piccolomini Library frescoed by Pinturicchio, the cathedral museum ‘Museo dell’Opera del Duomo’, the ‘Museo Civico’, the ‘Palazzo Pubblico’ … and the Piazza del Campo.


Overnight stay with breakfast in Siena

Distance: 82 km / 51 miles

Ascent & descent: + 1208m -1492m  

The first ring route in Siena takes place in the southern part of the Chianti area, there are no important climbs, but a continuous going up- and downhill… that will be felt in your legs at the end of the day. You cycle through the vineyards of Chianti Classico, the wine famous throughout the world for its excellent quality and the unmistakable black rooster brand. Along the way, many small villages such as Castelnuovo Berardenga, Castello di Brolio, Gaiole, Radda and Castellina will pass us. There are many stops possible: in Gaiole to visit the Eroica shop and see the extraordinary collection of vintage bicycles, Radda in Chianti, still enclosed in its medieval walls, is one of the most beautiful villages in Chianti together with Castellina. In Radda we recommend visiting the Chianti Classico Museum and the Porciatti Enoteca to taste some traditional products, while in Castellina we can recommend the Castellina ice cream shop in the town center.

For a wine tasting, you could stop at the Fonterutoli wine shop 4km outside Castellina in Chianti.


Overnight stay with breakfast in Siena

Distance: 96 km / 60 miles

Ascent/Descent: + 1745m -1750

Today’s tour develops in a southerly direction towards the Crete Senesi. You pedal along winding scenic country roads, in rolling sunny hills with ancient oaks, silver green olive groves and many vineyards. Highlight is the Brunello wine town Montalcino, which is reached after some steep climbs. The town, dominated by it castle (Rocca) is rich in history, has some nice museums and fantastic wine bars. After Montalcino you go to Buonconvento, another splendid town, where if you don’t want to make stop, just enter through the town gate and make a nice bike ride in the old centre past the Palazzo Podestarile with belltower, the Palazzo Comunale, the church of S.Pietro and Paolo of the 11th century and Palazzo Taja.


Overnight stay with breakfast in Siena

Distance 107 km / 66,5 miles

Ascent: + 1873m -1938m

You ride north where you meet the castle of Monteriggioni, which retains most of its thirteenth century structure. It is almost a must to stop here to make some pictures and to walk along the walkways of its walls enjoying the views. Continue to San Gimignano, declared a World Heritage Site by UNESCO, the center still enclosed by its original town walls, has characteristic towers and deserves a prolonged stop. It was an important town along the pilgrimage route Via Francigena. Now also well known for its Saffron production. Have lunch to taste a delicious Saffron risotto or a yummy asparagus flan with saffron cream. This divine dishes you could combine with a Vernaccia, the typical wine of the area. In the historic center there are many wine bars where you can taste these special wines and in Piazza della Cisterna you find the Dondoli ice cream parlour that won the award for best ice cream in the world.


Overnight stay with breakfast in Siena

Distance 95 km / 59 miles

Ascent: + 1238m -1238m

After breakfast ends this tour through a stunning Tuscan landscape.


Self guided tour
Difficulty level 4
Tuscany road bike tour from Florence to Siena
An 8 day tour through the Chianti

Florence-Mugello-Chianti-Siena-San Gimignano-Montalcino

Code | ITTOS03C

Typical hilly landscape with significant uphill and downhill cycling. There are sometimes steep climbs, but not too long. However, at the end of the day, a significant difference in level has been achieved. For the biggest part, you are cycling asphalted roads and some good dirt roads. Daily rides are between 82 km / 51 miles and 113 km /70 miles A tour for experienced road bike cyclists with a good physical condition.

Total km/mi: 493 km / 307 miles


Daily from April until the end of October. Note that during the Palio in Siena, it is more difficult to find availability and a supplement will be asked (on request).


2 or more people.


Florence / Siena

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