Eight days. Hundreds of kilometres. Plenty of climbing, a little gravel, countless coffee stops, a few missed turns, some very good wine, some even better food and, most importantly, a lot of time spent together.
We came to Tuscany to ride, but as the week unfolded, the riding became just one part of the story. The quiet roads, medieval hill towns, family-run bars, long lunches, local wines and those little places we somehow ended up returning to every evening all became part of the experience.
Here's how our first Tuscany tour unfolded, one day at a time.
Day 1: Our First Ride in Chianti
After travelling from Florence to Castellina in Chianti that morning, our base for the first three nights, we finally got on the bikes around noon. There were rental bikes to set up, saddles to adjust and a few last-minute tweaks before everyone was ready to roll.
Our first ride was a short introduction to the Tuscan roads, with a lunch stop at a local bar after about 15 km. Refuelled and ready to go, we soon found ourselves climbing back towards Castellina in Chianti. A gentle reminder that even a short ride in Tuscany comes with its share of climbing!
There was one little incident along the way. Amit had a small fall after his tyre skidded on some loose gravel on the tarmac. Thankfully, it was nothing serious, and by the evening he was doing fine and ready to get on with the trip.
In the evening, we headed into town for a tasting of Chianti Classico, followed by dinner. A good first day on the bikes, with plenty more of Tuscany waiting for us over the next few days.
Day 2: A Little Strade Bianche
A beautiful day in Chianti, and the only one on the tour that took us off the tarmac and onto what the Italians call strade bianche: the white gravel roads that have become synonymous with cycling in Tuscany.
We began with a coffee stop in the square at Panzano, accompanied by some local Tuscan snacks and biscotti. From there, a beautiful detour took us towards Lamole, with its fair share of climbing and lovely countryside along the way.
Then came the gravel. Seven kilometres of it. Some loved every bit of it, others weren't quite as convinced! Anand even managed a flat halfway through the stretch. A quick wheel swap, and he was back on his way.
Vandana, meanwhile, had decided to swap her regular road bike for an e-bike for the day. She seemed to be having a great time with it, especially on the climbs, where she had plenty of time to turn around and photograph everyone else working their way uphill.
By lunchtime, we rolled into Radda for some food, a few beers and plenty of banter. Ram and Srini were quick to declare the mozzarella quite possibly the best we'd ever had.
Little did they know that the real mozzarella winner was still a couple of days away!
After lunch, it was time to make our way back to Castellina. Later, we came together for aperitivo, sharing a few drinks and stories from the ride. It turned into one of those evenings that stay with you long after the tour is over, one of our most memorable in Chianti.
Day 3: The Climb to Volpaia
A shorter ride on paper, but certainly not short on climbing.
We rode towards Radda before tackling the climb up to Volpaia. As usual, Srini, Ravi, Sharad and Ram were the first to make it to the top, soon followed by Rajiv, Anand, Rao and the rest of the group. Some thought it was one of the most beautiful climbs of the tour, but everyone agreed on one thing: it was quite a challenge!
As the climb got steeper towards the top, Michelle, driving the support van, decided to play the devil on our shoulders, cheerfully suggesting to riders that they could take it easy, get into the comfort of the van and be driven to the top! Thankfully, nobody took up the offer.
A coffee stop in Volpaia gave us a chance to catch our breath before heading towards Lucarelli for lunch. And what a lunch it was! The food was memorable, but the cheesecake deserves a special mention. Quite possibly the best I've ever had.
There was just one small problem. We still had a fair bit of climbing to do, and we were heading out with full stomachs. With two route options available, the group split up, with some taking the shorter route and others opting for the slightly longer one. Eventually, everyone made it back to the hotel.
The day wasn't over yet, though. In the evening, we headed out for a wine tasting at a winery that was new to us, another lovely way to wrap up a day in Chianti.
Day 4: From Chianti to Siena
Today, we took the longer route to Gaiole in Chianti, the home of L'Eroica, the famous vintage cycling event that celebrates the old-school spirit of the sport, passing through Radda on the way.
After Radda came a long climb, followed by a long descent into Gaiole. Rajiv later told me that this was his favourite descent of the entire tour!
Francesco, our guide, was constantly going back and forth to make sure everyone was doing alright. When Venu Garu was struggling a little on the climb, Francesco stayed with him and, for the last few minutes, gave him the push he needed to make it to the top. That kind of support is easy to miss when you're looking at the ride from the outside, but it's exactly what makes having a good guide along so valuable.
The plan was to spend some time in Gaiole and stop for lunch before continuing towards Siena. Everyone made it to town, well, almost everyone!
Shyam somehow missed Gaiole altogether. By the time we realised, he was already 6 km down the road! He stopped for lunch at a roadside place, which, as he later told us, turned out to be pretty good, before rejoining the group.
Eventually, we made our way to Siena, our home for the next couple of nights. After some well-earned rest, we headed out on foot for dinner. And where else would you go on your first evening in Siena but the Duomo and the Piazza del Campo? A lovely end to a day that took us from the rolling hills of Chianti to the heart of one of Tuscany's most beautiful medieval towns.
Day 5: A Day Off the Bikes in Siena
After four days of riding, it was time to give the legs a break and explore Siena at a slower pace.
We had organised an afternoon walking tour with Marella, our local guide, who brought the city's history to life. We learnt about the magnificent Duomo, the famous Palio horse race and the traditions of Siena's contrade, the historic neighbourhoods that are at the heart of the city's identity.
We also visited the museum of the contrada that had won the most recent Palio, getting a glimpse into just how much these neighbourhoods mean to the people of Siena.
The rest of the day was left free to wander the narrow streets, linger over a coffee, enjoy a long lunch or simply find a spot in the beautiful Piazza del Campo and watch the world go by.
Day 6: Into the Val d'Orcia
If you asked the group to pick their favourite day of the tour, this one would be hard to beat. Almost everyone mentioned it afterwards as the best day of the trip, with Sharad and Rajiv going a step further and calling it the best ride of their lives!
We rode from Siena towards the Val d'Orcia, passing through Asciano and into the rolling hills and open countryside that make this part of Tuscany so special.
Francesco and Dario took care of the back of the group, making sure nobody was left behind. Even the coffee stop in Asciano involved a small detour off the main route, and they made sure everyone got through the turn and nobody missed the stop.
That stop gave us a chance to take it all in before we continued towards a local taverna for lunch.
From there, we rode on to Bagno Vignoni, our base for the next two days of riding. The landscape seemed to get better with every kilometre, and by the time we arrived, it was easy to understand why this day had made such an impression on everyone.
And then came dinner. After what many considered the best day on the bike, we sat down to what turned out to be the best dinner of the tour.
Some days just get everything right. This was one of them.
Day 7: The Road to Monticchiello
We had two routes to choose from today. One was the Pienza loop, while the other added a detour to Monticchiello: a steeper climb, but with some of the best views of the Val d'Orcia and, importantly, far fewer tourists.
Most of the group opted for the longer route. Rajesh and Shyam were in two minds for a while, but eventually decided to go for it too.
I thought the climb to Monticchiello was going to be a tough one, but at the top, most of the group, including Sharad and Anand, told me it wasn't nearly as hard as they had expected. Maybe five days of riding had made them stronger!
We stopped for a coffee at the top before descending towards Pienza, where the shorter-route group had already arrived. Bikes were parked, and they had started exploring the town on foot. We soon joined them before getting back on the bikes for the ride to the hotel.
But there was one more stop along the way. We pulled into a small, family-run winery for some olive oil and wine tasting, accompanied by bread and Pecorino cheese.
What made the stop special was the setting. The winery was right in the middle of a small village, tucked into what looked from the outside like an ordinary family home. The owners were incredibly warm and welcoming, and it felt less like visiting a winery and more like being invited into someone's home.
By now, we had also found our post-ride ritual. A small local bar near the hotel, Il Barino, had become the go-to place for everyone to catch up after a day on the bikes. Between the three evenings, we must have worked our way through more cocktails than we probably needed.
And leading the charge was, of course, Sandeep. He had somehow managed to turn Il Barino into his second home. By the third evening, I'm not sure if he was still a guest or had quietly become part of the staff. The cocktails were fantastic, the atmosphere was relaxed, and it became the perfect place to end another day in the Val d'Orcia.
Day 8: Montalcino
Another perfect day on the bikes, and one that came very close to Day 6 in terms of scenery.
The climbing started almost immediately, within 500 metres of leaving the hotel. We climbed towards Castiglione d'Orcia and stopped at the top, beside the medieval town, for a breather and, of course, a few pictures.
After another hour and a half of riding through beautiful countryside on almost completely empty roads, we stopped for coffee. By then, I had to scratch my head and wonder how many cars had actually passed us since we started riding. Not many!
We were the only customers at the small family-run bar when we arrived. Just as we were getting ready to leave, a local family walked in, turning our quiet little coffee stop into a slightly busier one. The owners were lovely and made us feel very welcome: exactly the kind of place we enjoy finding along the route.
The final leg took us towards Montalcino, the home of Brunello. Lunch was inside a medieval castle, with a glass of Brunello to go with it. It was our last lunch of the tour, and it couldn't have had a more spectacular setting.
Another beautiful day on the bike, another reminder of why the Val d'Orcia had quickly become a favourite with the group.
In Srini's words
Srini has ridden with us since 2017, and Tuscany was his twelfth tour. This is the week in his own words.
It’s difficult to pick one particular ride, but riding through the Tuscan countryside and its small villages was incredibly memorable. We would ride up to these little fortified towns, stop for a break and walk around within the old city walls. There was something magical about it: you almost felt transported back in time. What struck me was how well these towns had retained their character while still having shops, restaurants and everyday life going on inside them. It made the whole experience feel very authentic.
The lush green hills were beautiful every time we rode through them, but what really stayed with me were those moments when the landscape suddenly opened up into these enormous rolling hillsides: acres and acres of open land, with rows of cypress trees leading up to these magnificent old villas and estates. That combination is so distinctive to Tuscany, and seeing it from a bicycle made it particularly special.
I find it difficult to compare one cycling tour with another, because every region has its own landscape, culture and character. One thing that really changes the experience each time, though, is the local people who ride with us and support the tour. This time we had a wonderful group of Italians driving the support vehicles and riding alongside us. On those long rides you end up having lots of conversations, and you get a glimpse into how people actually live, how they see their own country and even how they see the world. There’s also an interesting cultural exchange that happens. Almost inevitably, we’re the first Indian group that the local riders have spent this much time with, so there’s curiosity on both sides. That interaction with local people adds a lot of character to every tour and, for me, is a big part of the experience.
Off the bike, one of the highlights was definitely lunch on the final day. It was set up inside a castle, accompanied by some of the region’s famous local wine. After several days of riding through this landscape and seeing these historic places from the road, actually sitting down for lunch inside a castle was a pretty extraordinary way to finish the trip.
As for the food, surprisingly, it was the mozzarella. I thought I had sampled enough cheeses over years of travelling to different countries, and of course I’d eaten plenty of Italian food before. But one day we were served this incredibly simple mozzarella, and I remember deciding that it was probably the best cheese I had ever eaten. Then, just two days later, we had a lavish dinner at our hotel and they served mozzarella again, and somehow that one was even better! That really summed up the food in Tuscany for me. It wasn’t necessarily about elaborate dishes. The quality of even the simplest ingredients was incredible, and something as basic as fresh mozzarella could end up being one of the most memorable tastes of the entire trip.
Srinivas Pratapa
And that was Tuscany
Eight days of riding through Chianti, Siena and the Val d'Orcia. We came for the roads, but somewhere along the way, we also found our favourite coffee stops, our favourite bars, our favourite lunches and, apparently, Sandeep's favourite cocktail bar.
There were climbs that looked harder than they turned out to be, gravel punctures, missed turns, bottles of wine, long lunches, very good dinners and plenty of laughter along the way.
Most importantly, we came as a group of riders and left with a collection of stories that will probably be retold for a while.
For us at Barnowl, that is what a cycling tour should be about. The riding matters, of course. But so does everything that happens between the kilometres: the people you meet and the places you discover.
The full itinerary is on our Tuscany Cycling Tour page, and more photographs from the week are in the gallery.
Written by Krish.
