Tuscany Cycling Tour from Florence to Siena
The views along the road as we cycled through the Chianti Hills towards Sienna.
Sunshine. 42 degrees, feels like 50 degrees.
Continental Europe was in the midst of a heatwave and, peeling the sheets off my sticky legs in our hotel room, I could feel nerves building in the pit of my stomach.
When planning our summer holiday there was a decision I got stuck on for weeks. Graeme is a keen cyclist and I knew he would relish the chance of a day devoted to hiring bikes and getting out into the Italian countryside - a Mecca for cycling. But I was desperate to visit Siena, a very achievable day trip from our base in Florence. What to do?
A Cycling Tour from Florence to Siena
Step in ibiketuscany. Discovering their tour of a ‘soft’ ride from Florence to Siena seemed like the perfect solution. Beautiful Italian bikes, undulating terrain suitable for beginners like me, and a long road flanked either side with vineyards. A short drive out of Florence into the villages of the Chianti Hills would be followed by 13 miles cycling (with a van supporting us in case of any difficulty), and then an afternoon free to spend in Siena. From the comfort of our flat in a very wintery UK, 13 miles in the sunshine sounded like something I - a cycling novice - could achieve.
We even did a practise ride of 26 miles around Rutland Water. Maybe I’ll write another post about that, but for now it’s enough to say that I didn’t love it, but I finished it. So 13 miles would be easy… Only there’s one thing I didn’t foresee.
Feels. Like. Fifty. Degrees.
The Drive to the Starting Line
Sweat dripped down my spine on the short walk along the Arno to where our guide, Suzie, was meeting us. After a short wait she pulled up in a silver van and beckoned us in to the glorious, air-conditioned interior. Suzie was probably the best guide I’ve ever had on any excursion. She was easy to talk to and we were soon finding out more about her and her cycling background. Graeme was happy to speak to someone who could ‘talk bikes,’ and she even picked up on my hesitation, reassuring me that the air would be cooler out of the city and she would never be far away in the van if there was any trouble. She explained the bikes and the route we would be taking, the villages we would stop and rest in - and even an unexpected wine tasting that was including along the way.
Our first stop was to pick up a family who would be joining us on the ride, but it turned out only one of them was braving it. On the drive it was decided that Dmitri, our Russian companion, was an experienced cyclist and would ride a bit further than we would. We would drop him off in the village of San Donato in Poggio, where we got to walk around as Dmitri saddled up and got on his way.
Suzie was confident Dmitri would be meeting us in no time as the incline wasn’t too steep. As we made our way up the winding roads on the short drive to Castellina, I was grateful to be in the van rather than on a bike… my nerves grew again as I questioned her judgement of what qualifies as ‘steep’.
Getting on our bikes in Castellina in Chianti
We had some time to walk around Castellina in Chianti whilst our bikes were prepared. It is a picture perfect village. We wandered through the town and along the ancient walls, where there is an underground tunnel we walked through to escape the increasing warmth of the day. Along the way, small windows gave us a sneak preview of the spectacular views we would be treated to during our ride.
We walked through pretty courtyards full of flowers and back down the main street where shopkeepers were opening their doors. This really is the heartland of Italian cycling. I watched Graeme rush from shop to shop like an excited child at Christmas, pointing out different jerseys from iconic Italian racing teams. I don’t know much about cycling, but the retro designs and bold colours looked stylish in that classic Italian way. He bought a hat and put it straight on his head as we walked back past the church to begin our ride.
The Open Road: Cycling through Tuscany
It was finally time for us to ‘saddle up’ and be on our way. Suzie pointed us down the road and told us she would wait for Dmitri then catch up with us. Our next stop was straight downhill to a village called Fonterutoli.
The first few minutes I was looking down at my handlebars. I eyed the gears with suspicion, cringing as cars whizzed past. I felt like I had to concentrate on keeping in a straight line. I heard Graeme calling from behind me, telling me to look up, look at the view. When I finally listened to his advice, the nerves melted away.
Either side of us, lush green vineyards stretched as far as the eye could see, rolling up and down into the distance. The road cut a harsh line through the landscape. It’s like we were travelling through a painting, two lonely cyclists and nothing but romance of the open road. Once I found my rhythm everything moved with ease; I stopped flinching at passing vehicles, instead enjoying the occasional classic car that passed, and even gave thanks for the oppressive heat of the day which became a cooling presence when were were on the move.
We saw the silver van parked up on the side of the road and I rolled into Fonterutoli with my confidence sky high. Catching our breath and gulping cold water, we heard the history of the place we had stopped, a small hamlet perched in the hills. It is a wine-lovers’ paradise; a collection of buildings erected by a noble family to dedicate to wine-making. Down the hill through the haze of the rising heat, Siena is just visible.
A pretty doorway in the village of Fonterutoli.
From Fonterutoli to Siena
We walked around the empty streets before being ushered into an enoteca for our included wine-tasting. Inside, a friendly sommelier told us more about the history of the area and the wines. We tasted five different labels - very small tasters as we still had miles to go on the bike! It was wonderful to get a taste of the area and a well appreciated rest for the legs.
Back on our wheels, Suzie led us down the hill and on our way. We made our way towards Siena, stopping every few miles for water or, more often, for pictures, because it was hard to believe the view. At any point a directional decision needed to be made we would see the silver van to point us the right way.
The ride itself was mostly unchallenging, except for one climb which the cyclists said was short but I disagreed. I struggled up half way before giving myself a break, only to realise that was a mistake. I had lost all my momentum, and that second half of the hill felt like an eternity.
Stopping for yet another picture by the roadside.
Our journey came to an end as we sped downhill to a roundabout which signalled the approaching traffic of the city. We pulled to the side of the road and piled the bikes into the van for the short ride into the centre of Siena. Agreeing the return meeting place and time we headed off to explore the medieval city I had so wanted to visit, the van awaiting our return to drive us back to Florence later that evening.
Our Tuscan Cycling Tour Experience: Florence to Siena by Bike
There is so much I love about Italy and about Florence but for me, the non-cyclist, that day is the highlight of all the time I have spent in the country. Suzie’s knowledge of the area and her friendly, encouraging and enthusiastic welcoming of our mixed abilities meant that we all managed to have a wonderful time. For me, exploring those small medieval towns, drinking wine, taking the time to slowly watch the landscape change as we rode through the hills, breathing in the fresh air and enjoying the silence of a beautiful summer’s day are things I will always treasure. The afternoon in Siena was the icing on the cake - or, should I say, the parmesan on the pici - but I will save that delicious tale for another blog post. Maybe there’s a cyclist in me, after all.
How to cycle from Florence to Siena - beginner friendly!
We loved every moment of the tour with ibiketuscany and 100% recommend them. We took the ‘soft’ version, which I would say is suitable for people like me - general fitness ok but not a regular cyclist. There are loads of other options for rides in the area and we can’t wait to go back and try a few more.
If you are a less serious cycler, there are lots of cycling tours available outside of Florence in the Chianti Hills. Have a look at Get Your Guide* to book something that suits your holiday style!
*Affiliate links. If you click this link and book we will earn a small commission. There will be no extra cost to you!
Related Content
Pin this blog post to read later…
