
A bikepacking trip from San Miniato to Siena
48 hours cycling tour along the Via Francigena
We never have enough time. We spend years planning trips that we never actually make. This idea, which I believe is widespread, is based on the idea that cycling takes a lot of time. We look at social media and photos of people doing trips that last for months, but we don’t realise that we can get on our bikes before the clock strikes the next hour.
Not long ago I found that you can load a bike with minimal baggage and, only forty minutes from Florence, embark on 48 hours of pure nature and culture. For those who maybe don’t know it, an ancient road unfolds over the cypress-stippled hills between San Miniato and Siena, taking pilgrims from every corner of Europe towards Rome. I am talking about the Tuscan Via Francigena. This route, traditionally a footpath, can also be done on a suitable bicycle: a mountain bike, for example, a gravel bike or even a touring bike adapted for dirt tracks.


From San Miniato to Gambassi Terme, from vineyards to clay hills
Early, but not too early in the morning, I heft the panniers onto my bike frame and check the brakes. I oil the chains and try to think of anything I might have forgotten for a night away. Once the bike is ready, a smile spreads across my face, and I make for the train station. It only takes forty minutes by train from Florence, and thanks to the regional services transporting my bike is both ecological and sustainable.
Getting off at the little station of San Miniato, I switch on my GPS navigator, and treat myself to a lavish breakfast at a nearby bar. I’m immediately on the Francigena and climbing up to San Miniato, a tarmac surface but fairly steep. This is not any pedestrian road, but a pilgrimage route, where joy and fatigue have always gone hand in hand, inseparable.
The view from the hilltown over the Fucecchio plain is breathtaking. I cross the main piazza and thread through the narrow streets, which run together into a road, at which point the houses end. It’s just me, the hills and my bike, mere minutes after setting off. A few kilometres on, a U-turn compels me to exchange the road for a dirt track and start the real point of my excursion. The wheels begin to squeak on the stones, the vibrations get stronger, and the handlebars become more fun to handle. One at a time, vineyards, olive groves and farmsteads which hark back to the time of Grand Duke Leopold come into view.
On this first leg of the journey, up to Gambassi, your wheels almost never touch asphalt. There is one stretch of it running through a vineyard, and in rain it becomes a little greasy, but the rest of this section is pure dirt track; paths really, but all completely manageable. There’s one portion, which I won’t locate precisely lest I ruin the surprise, where I find myself in front of hills with a high concentration of clay: in spring, the dark earth brings forth flowers of every kind, and the steep slopes resemble a meadow. At the end of summer, meanwhile, the overturned fields are bare and brown and absorb all the light except that reflecting off the road, which, being made of a lighter, more compacted earth, is visible among the dunes. The route is lined with abandoned houses, which somehow makes this journey even more introspective, and finally I can feel the silence that I’ve been longing for, impossible to find in the city.
The dirt track comes to an end and a length of asphalt takes us towards Gambassi Terme, via the Pieve di Santa Maria a Chianni and the Ostello Sigerico. We have to scale one more hill before we arrive, but I strongly recommend stopping to have a look at this enchanting place. The structure of the Ostello, apparently very old, has an internal courtyard which leads into a garden studded with ancient olive groves. Here you have a stunning view of the village of Gambassi.
The managers of the Ostello are hospitable people, and you can charge your batteries here if you’re travelling by E-bike, or have a coffee and recharge yourself after the climb. Back in the saddle, we come to the church of San Jacopo and Santo Stefano, which I highlight for two reasons. Firstly, you can see how the building has been restructured over the centuries, its Romanesque origins being replaced by a nineteenth-century pastiche of medieval glory. And secondly, in front of this church I ate one of the best porchetta schiacciatas that I’ve had on my various Tuscan trips. I made a mental note to tell you about it, because by the time you arrive at this church your greatest desire in the world is to munch on something.


From Gambassi Terme to San Gimignano, the city of towers
Leaving the town and heading for the hills, the road disappears again. More dirt paths await you. A bike laden for a long journey would quickly become a burden, but mine, which I’ve loaded with a minimum of equipment, is perfect for this route. Always remember that in these situations, some bikes are more rideable than others: even with light luggage, the front wheel tends to steer much more sensitively. What strikes me, leaving Gambassi Terme, is how the land changes almost completely. With every valley that I conquer, I find a different type of forest; the panoramas mutate with extraordinary speed. By now I’m almost at San Gimignano, which well deserves its nickname of the city of towers. There’s nothing better than seeing the Torre Rognosa, which used to be a prison, and its little sisters gradually swelling in the distance, puncturing the horizon. Seeing them up close, at the end of this stretch, I ask myself how they managed to build towers so slender and so tall, guardians and beacons of the Sienese valleys. It is truly amazing how a city like this has been able to withstand time. I recommend exploring it by foot, given the number of tourists within the walls.
The sun is setting, but luckily I’ve arrived at the Pilgrims’ hostel. My journey begins anew tomorrow. I think about the landscapes outside; I think about how close my city of sirens is, but at last, I feel far from home.


San Gimignano to Monteriggioni: the way of a medieval knight
The section that takes you to the ‘castle city’ is maybe a bit more demanding. I leave early enough to find snow covering the valleys, which can now be said to be Sienese valleys. The paths that lie before me are more earthy now, the hills lower but with no lack of ups and downs. I have to ford a little stream at one point, on a fairly steep bit of track: with a good bike you can do this no problem at all, but I stress the need to always be careful when fording a watercourse. My advice with them, as with flooded patches of road, is to select a low gear and just keep pedalling. In most cases, there will be more worry than real danger, as you’ll be on the other side in a matter of seconds. And if it doesn’t seem to be going well, don’t hesitate to dismount. Your shoes will dry as you pedal on.
The land changes between the provinces of Florence and Siena, famously becoming redder and denser, helping the tyres grip and making descents even more fun. On the approach to Monteriggioni, I note Abbadia a Isola, a little monastery-village that seems to be tucked away to the right of the road. Every September, this Romanesque monastery plays host to the Slow Travel Fest, which I recommend wholeheartedly. Once you’ve reached this place, Monteriggioni and its circuit of fortified walls are closer than the horizon.
One last stretch of dirt track lies between me and a hard slog up to the town, but once I’m through the north gate of the citadel I feel like a knight finally come home.


From Monteriggioni to Siena, home of the Palio
The final leg on the journey to Siena is done on asphalt, but I would say that after miles and miles of loose track, especially that section leading up to Abbadia a Isola, a bit of asphalt is no bad thing, not least because the curvilinear road leads directly to Siena’s Porta Camollia.
After a dozen kilometres or so I’m in the hometown of the Palio. Siena might be the most medieval city in the world, thanks to its streets, old houses and marble churches. Taking these roads to Piazza del Campo is an adventure that has little to do with my typical weekend. I won’t wax lyrical about the extraordinary marvels of Siena; I’ll just advise that once you’re through the gates and have locked up your bike – most of Siena is pedestrianised – you should make straight for Piazza del Campo. I think about the centuries past, and beneath these palazzi, I feel part of them.
At the Siena railway station I get on one of the regional trains, bike in tow, and head home, thinking about how in only 48 hours I’ve sated my wanderlust. It’s usually hard to quell, but with this trip I’ve certainly calmed it a bit.

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