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From Bologna to Chianti

The spectacular cycling tour to this almost hidden landmark known as Chianti, was reason enough to visit Tuscany. The panoramic roads that wind throughout the hills of Chianti and Elsa valley hold many surprises. I came back with a new awareness, I must arrange another trip and choose other paths, because in this region there is so much to see, so much to discover.

I wanted to reach Florence starting from Bologna for some times, it’s about 100km that cross the Apennines between climbs and descents. The idea of ​​connecting two such iconic cities in one day of cycling fascinated me from the first moment I moved to Bologna. This was a weekend arranged at the very last minute. A friend from France was coming for a cycling tour in Tuscany and I could meet him in Florence, while another friend had a spare day and he could ride with me from Bologna and then I would have had one day left to return from Siena to Prato again in solitude. The bike was ready, the bags of the bikepacking full with the tent, the winter sleeping bag, some cloths and off I was ready to go.

Day one: Bologna – Passo Raticosa – Passo Futa – Fiesole  (112  Km – 1,730 Elevation – Sunny)

Starting from Bologna there are at least 5 different way to get to Florence, the choice fell on the road that from Val D’Idice passing through Monterenzio from San Benetto del Quercieto reaches the summit of the Raticosa Pass with a constant climb between 6 and 7% in 14km. The arrival towards the border between Emilia Romagna and Tuscany was preceded by a first part of the climb that opens the view on the valley below and on the Caverenno cliff (Rocca di Cavrenno) with its village, below that a feudal fortress of the Ubaldini family, which for centuries has regulated the passage of travellers between the two regions. From the Raticosa pass the gaze and the road continued rapidly towards the Futa pass, from there our road went downhill up to Galliano where our track was taking us on an unpaved road. Since we had many kms ahead and one of our bicycle was a race bike, we decided to go back on the main road that for about ten km became a bit trafficked, at least up to the crossroads with Borgo San Lorenzo, when we found ourselves in a minor road that climbed gently up to to the Vetta delle Croci at the gates of Fiesole. We reached Fiesole downhill, time to stop at the local supermarket and reach the Camping Village, a quiet place with Bungalows and a magnificent view of Florence, perfect for enjoying an aperitif at sunset stealing a spot in a terrace of a closed bungalow, because the tables around the swimming-pool were already closed for the season. The campsite wasn’t crowded, there were some Germans’ couples who were travelling with vans, but the restaurant was empty. Unfortunately the restaurant was not only empty of customers, but also of hospitality, the staff seemed tired and bored listening to our needs. Anyway, it didn’t take much to us to enjoy the evening, the view, a nice chit chat with friends, a homemade pasta with tomato sauce and the inescapable bottle of Chianti.

Check on Komoot the tour gpx.

Day two: Fiesole – Firenze – Chianti – Siena (96  Km – 1,560  Elevation – Sunny)

Starting again from Camping Fiesole our day had a completely different flavour upon arrival. The clouds had covered Florence, the road downhill to the center of Florence was cold and damp. However it was only a moment, because when we arrived in the centre of the city the sun had already pierced the clouds, the “must have” photo in Piazza della Signoria, the passage over the Ponte Vecchio, Florence wasn’t crowded, it was stunning! We would have soon left it to head towards Chianti hills. Chianti was a fixed destination for me, I used to go there every year since I started enjoying Eroica and the dusty roads of its competition. This year instead we stayed on asphalted roads and in addition to the hills we climbed Valico del Morellino, another of those climbs that without the full load of tent and bikepacking, would have been easy, but instead it became challenging and slow because of that. Our route through the hills became more typical immediately after the pass when in the direction of Greve in Chianti we entered the hills among its ups and downs, not always easy, with 18% stretches and equally challenging descents. In Greve where I used to stop for refreshment during Eroica, we also stopped and refilled our bottles, before continuing towards Val D’Elsa and then Siena. For all this part of the road I think I stopped every 2 kilometres to take a photo and then another, the views of the vineyards and the colours of Tuscany, impossible to let them flow without immortalising them. Getting to Siena, especially in Piazza del Popolo was not easy, the streets were crowded with people, moreover in the center of Siena you cannot go by bicycle. We had to push our bikes to the square for the inevitable umpteenth photo. From there the Camping Colleverde chosen for the night wasn’t far away, we went out of the city to the hill and we managed to pitch our tents still under the sunset’s lights. For dinner, we enjoyed a pizza at the campsite restaurant in a relaxed and pleasant atmosphere, typical of the Tuscany I imagined to find.

Check on Komoot the tour gpx.

Day three: Siena – Chianti – Prato (91 km – 880  Elevation – Sunny)

The awakening in Siena was fresh and humid like the one in Fiesole, time to pack up the tent and have breakfast, separate our roads and with my bike I headed towards Colle Val D’Elsa, immediately the view was like one of the typical romantic Chianti landscape; hills, vineyards, villages. Colle Val D’Elsa was one of those, internationally renowned for the production of crystal glassware since the Middle Ages. The road continued pleasantly between ups and downs up to Poggibonsi, when I followed a narrow road that immersed itself in a valley allowing me to look at the hills this time from below. It has been an easy ride, it gave me the opportunity to stop for a quick visit in also in Barberino Val D’Elsa, a village that in the past used to control with its strong walls one of the access roads towards Florence. Views and atmosphere were pleasant up to Fiano, when the road became more “suburban” in the direction of Prato.

The spectacular cycling tour to this almost hidden landmark known as Chianti, was reason enough to visit Tuscany. The panoramic roads that wind throughout the hills of Chianti and Elsa valley hold many surprises. I came back with a new awareness, I must arrange another trip and choose other paths, because in this region there is so much to see, so much to discover.

Check on Komoot the tour gpx.


TOTAL BUDGET 3 DAYS ALL INCLUSIVE: 69 euro

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