Tuscany road bike tour from Florence to Siena

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 11^th 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.