Glorious Gravel

Off Roading: Tuscany

The undisputed home of gravel cycling just happens to be one of the world’s great destinations with incredible food & delicious wine. Another tough assignment for Max & Simon to go and explore as they take on all that Tuscany can throw at them over a long weekend…


As much as we all love gravel riding in the UK, there’s one place we always dream of after one too many muddy bridleways, Tuscany. Every spring I sit down to watch Strade Bianche, one of my favourite races of the season and am left amazed at the perfect ‘white’ gravel roads, they’re even riding it on road bikes! Back in June myself and Simon set out to explore this gravel paradise and of course sample all the food and wine along the way.


Similar to other recon trips, every beautiful ride abroad has to start with a trip to one of the lovely ‘London’ airports. It had been a more hectic few weeks leading up to the trip, the three days proceeding consisted of a 9 hour flight from Thailand, immediately working two days at our Surrey gravel event, one day of rest and then an early morning trip to Stansted.


On arrival in Pisa we were collected by our local colleague Ingo who had been organising this epic route for us. He went through what we had in store and told us a few stories about his race walking days and his incredible 10k walking time (39 minutes!). Unfortunately Ingo was guiding another group, so after dropping us off at the hotel we were on our own for the next four days.

Stage One: San Gimignano to Siena







Ingo had warned us to set off early to avoid the worst of the midday heat, but of course we traded sleep for comfort. After a hearty breakfast and a few bike issues, it was 10am when we got started and it was already getting toasty, we had 95km ahead of us but we had smiles on our faces as we got our first glimpse of Tuscan gravel and the stunning views of the Italian countryside.


The ride today came in two parts, the first half wasn’t on ‘white roads’ but on more classic gravel tracks, whilst not what you expect when you think of Tuscany but they still wound us through old villages and picturesque farmland. The second half of the ride begins after the main climb of the day, 4km at 7% on gravel, at the top we were both drenched in sweat and wondering why we didn’t heed Ingo’s advice. Alas there was a fountain at the top and we drenched ourselves in water and carried on.


The terrain on the rest of the ride would prove easier but our legs seemed to be saying otherwise. Our lunch stop consisting of bruschetta and fanta, whilst delicious, didn’t seem to be providing the sustenance required for 6 hours in the sun. The constant vistas and our first white roads made us soon forget about our empty legs, the gravel is truly as good as it looks on the TV and the white roads constantly roll up and down, offering another spectacular view over each mini summit. We soon had our first glimpse of Siena, on the home straight now, we ploughed on. After a little bit of thought, we realised Siena was perched at the top of a hill, what’s one more climb on tired legs? One climb too many it seemed, we arrived in Siena and slumped outside a supermarket, maybe June isn’t the best time to ride in Tuscany. An absolutely stunning day though, and a great introduction to riding in this gravel paradise.

Stage Two: Siena to Radda in Chianti







After an evening walking around Siena, some delightful pasta and a glass of Chianti we were ready to do it all again. The next day we would be following the L’eroica route for the most part, whilst the stats looks more difficult, it would be on perfect gravel tracks all day… bliss. We went to bed with the full intention of an early start to avoid another baking from the sun. After a hotel breakfast, a trip to the bike shop and a supermarket run it was suddenly 11am and we were again getting ready for another day in the sun. 


The L’Eroica is a permanent signed route around Tuscany, which is 209 km long and usually completed on vintage road bikes with narrow tyres and small gear ratios. Fortunately we were neither riding the full 209km nor had we had come equipped with wide gear rations and nice wide tyres. The route started with the same section we had ridden yesterday but in reverse, knowing that it would be constant white roads today, we were in for a treat. The route did not disappoint, stunning views of rolling hills, olive groves, and vineyards.


The landscape is also dotted with charming towns and villages, each with their own unique character. Although our legs hurt, we never really noticed as each hill seemed to treat us to a view better than the last. Our ride finished in Radda in Chianti, set on a hilltop amongst a sea of vines, the mediaeval town is typically Tuscan. Small cobblestone lanes meander up past quaint buildings, which sit stacked atop each other. The perfect spot to savour the ride and enjoy a glass of chianti.

Stage Three: Radda to San Gimignano







Our third and final day on the bike would be slightly different to the previous two days. We hadn’t yet tackled many long climbs, the L’Eroica route is characterised by constant rolling terrain, whilst certainly not flat you are never on one climb for that long. Today would feature 3 longer climbs and less punchy terrain, much easier to get into a rhythm. After the first climb we had almost 25k of rolling downhill and it was easily some of the best riding of the trip, after a quick coffee stop we were soon on the next climb and ticking off the K’s.


I previously mentioned that myself and Simon were riding this trip unsupported, we were fortunate enough to have someone transporting our luggage for us but other than that we were on our own… So, as we approached the top of the second climb of the day I managed to pick up a puncture, no biggie, we had everything we needed to fix it. I got the tube out, found the culprit in the tyre and put a new tube in and went to pump it up using Simon’s pump. ‘Does this pump work Simon’, after 10 minutes of fiddling, clearly not. The next 30 mins were spent waving down cars until one kind Italian man stopped and helped us with a track pump (I’ll also pack my pump next time). The rest of the ride went smoothly and before long we were back in Sam Gimignano and it was almost downhill all the way back to the hotel.

The arrival beer at the hotel had never been so welcome, myself and Simon both put our bikes to the side, sat by the pool and reminisced on a fantastic trip through Tuscany. Whilst I don’t think any cyclist would need much convincing to head to Tuscany for a gravel trip, the region did truly live up to the hype. The best trails, sublime vistas and of course some of the best wine and food in the world.




A quick shout out to the 30 legends who took part in the first Off:Roader Toscana with us in Oct 2022. One of the best long weekends we can remember full of big days on the bike and laughter filled evenings 🍷

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