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 Gran 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.
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 Classico dei colli Fiorentini watching all the people passing by and be happy you are in this one of a kind town.
Today's excursion, the middle stage of the Florence Granfondo, takes you through an enchanting hilly landscape with two climbs of more than 800 m and a further two of about 400 m each. The Mugello area is famous for pastures and knife production. The small town of Scarperia is worth a visit.
It won't be easy to abandon Florence, but Chianti is awaiting you with a completely different landscape, with some hilly areas, but also others with woods and vineyards stretching to the horizon and a number of climbs up through higher almost mountain-like hills. If you haven’t already visited a winery, then this and the next itinerary are still excellent opportunities. In Chianti, you can still find fascinating historic villages such as Panzano, Radda in Chianti and Gaiole, to name just a few of the places worth visiting. In Gaiole, you encounter the permanent circuit of the Eroica, a cycling event with classic racing bikes that takes place every year along the region’s characteristic dirt tracks, evoking the bicycle racing of long ago with its purity of intention and contact with nature. The Eroica’s route takes us across Chianti Classico to Brolio Castle, jewel of the estates owned by the Ricasoli family, with magnificent panoramas and excellent wines. You ride down through the vines towards Siena which appears on the horizon, a postcard of presentation for this magnificent city
The first tour of the Siena area crosses the south of Chianti Classico area. There are no great climbs, but a constant series of ups and downs which you can feel in your legs at the end of the day. You ride through the vineyards of Chianti Classico, the world’s most famous wine for excellent quality and the unmistakeable black cockerel logo.
Along the route there are numerous small villages such as Castelnuovo Berardenga, Castello di Brolio, Gaiole, Radda and Castellina.
At Gaiole, a visit to the Eroica shop with its extraordinary collection of classical bikes is a must, while Radda in Chianti, enclosed in its medieval walls, is one of Chianti’s most beautiful villages, together with Castellina in Chianti. We recommend you visit the Chianti Classico Museum and Enoteca Porciatti wine bar and shop in Radda, perhaps for a snack with traditional products, then the Castellina ice-cream shop in the centre of the village with the same name.
For a wine tasting, a visit to the Enoteca Fonterutoli wine bar and shop, 4 km after Castellina in Chianti, is mandatory.
The day’s excursion heads south towards the clay hills of Siena. You often seem to be riding through a moonscape, the vegetation is different, but there is no shortage of olive groves and vineyards. You cross the area famous for producing Brunello wine, then after a brief but steep climb, come to the village of Montalcino, steeped in history and full of wine bars and shops. Impossible to offer advice on where to go for a tasting as all the wine is good here. Just go into the wine bar that appeals to you most and ask what they recommend.
After Montalcino, you come to Buonconvento, another splendid village where, even if you don't want to actually stop, it is still worth entering inside the walls and visiting it by bike.
The towers of San Gimignano and the famous Vernaccia
Pedaling in a northerly direction, we come across the castle of Monteriggioni, still with much of the 13th century structures. A photo and a visit to the walkways along the walls are mandatory. You continue to San Gimignano, a UNESCO World Heritage Site, where it is worth lingering to visit the town centre enclosed in its walls with its characteristic towers.
Here the typical wine is Vernaccia, one of the few whites in an area dominated by reds. In the city centre, there are numerous wine bars and shops where you can enjoy a tasting, while the Dondoli ice-cream shop in Piazza della Cisterna has won the prize for the world's best ice-cream.
Waste no more time
Do not hesitate to ask for more information and plan now your holiday