Val d’Elsa gravel cycling experience
One of the most authentic areas to ride in Tuscany
I was born and raised in a small town in Tuscany.
At twenty three, I left Italy to complete my studies and start my career in Industrial Design in London, England where I eventually stayed for more than eight years. It was there, somewhat unexpectedly, that my passion for cycling truly began.
Other chapters followed: the Netherlands, Argentina, and long journeys with my bike as a constant companion. Eventually, I came back home. Rediscovering Tuscany felt like a revelation. Some people are surprised when I say that I had to leave Italy to fall in love with cycling, but sometimes distance is exactly what allows you to see things clearly.
I still remember my first winter back. The light, the landscapes, the quiet roads stretching through the countryside. Riding felt natural, almost inevitable.
Out of that renewed curiosity and passion, Asimismo, my bike touring agency was born.
Riding local: Val d’Elsa
Today, I live in Gambassi Terme, in Val d’Elsa, an area of Tuscany that I know intimately, not only as a destination, but as home.
I ride these roads every day, in every season, watching the landscape change with the light, the weather, and the rhythm of rural life.
The Val d’Elsa sits between Florence and Siena, yet it remains surprisingly untouched by mass tourism. It is a place where medieval villages, rolling hills, vineyards, and cypress-lined roads coexist in perfect balance. For cycling — especially gravel cycling — it offers something increasingly rare: authenticity.
The view of Montaione and the mountains behind after a day of snow - January 2026
An authentic Tuscany, best discovered by bike
San Gimignano, Certaldo, but also Gambassi, Montaione and the surrounding countryside form the heart of the Val d'Elsa experience. Here, white gravel roads connect hilltop towns, farms, and ancient paths that have been used for centuries. Traffic is minimal, the pace is slow, and the silence is often broken only by the sound of tires on gravel.
San Gimignano is the one everyone knows – those famous medieval towers you can spot from miles away. Yes, it gets busy during the day, but arrive by bike early in the morning or late afternoon and you'll have a completely different experience. The narrow streets empty out, the light hits the old stones just right, and you see locals doing their thing. The best part? Tacking the surrounding white gravel roads is real fun and the view of the skyline in the distance something unique. By following us on our guided bike tours you will get views that people stuck in tour buses will never see.
Certaldo is actually two towns in one. There's the newer part down in the valley, and then Certaldo Alto up on the hill – the old medieval village where the writer Boccaccio was born, a real jewel. You can take a small cable car up or pedal your way to the top if you're feeling strong. The whole upper town is made of red brick, really beautiful and way quieter than San Gimignano. A lot of my clients end up saying this was their favorite stop because it feels more real, less touristy, and with us you will approach it from a unique side.
Gambassi Terme doesn't get much attention from guidebooks, but that's exactly why I like it. People have been coming here for the thermal baths since Etruscan times. It's a working town – you know, actual locals living their normal lives, not just shops selling souvenirs even tho like Montaione has a lot of Agriturismo’s spread along its municipality. The gravel roads around here lead you to old farmhouses, tiny churches nobody visits anymore, and spots where you can see across the whole valley. Stop at the local bar and you might end up chatting with someone who remembers when these dirt roads were the main roads.
Montaione rounds out the group. It's an agricultural town that's kept its character – good local food, some nice craft workshops, nothing fancy. But the countryside? That's where Montaione really shines. You've got everything here: forests, wheat fields, vineyards, those classic cypress tree-lined roads. The unpaved roads around Montaione are some of the best for cycling in the whole area. You can pick easy routes or tough ones depending on which direction you go.
From my rides, I can honestly say this is one of the most genuine areas in Tuscany to explore by bicycle, far from postcard clichés, yet deeply rooted in Tuscan identity.
Many of my routes naturally extend toward Volterra. It's not technically part of Val d'Elsa, but it's close enough and connected to the same landscape. Fair warning: getting to Volterra means climbing. But once you're up there, it's worth every meter. You've got artisans still carving alabaster the traditional way, Etruscan walls older than Rome itself, and on clear days you can see all the way to the coast.
Why Val d’Elsa is ideal for Gravel Cycling
A dense network of strade bianche and secondary roads.
Continuous rolling terrain, never extreme but always engaging.
Landscapes that feel lived-in, not staged.
Small villages where time moves slowly and hospitality is sincere.
Ancient pilgrim routes used centuries ago and still magnificent to ride with a gravel bike
This is cycling for those who value experience over performance, beauty over speed, and connection over conquest.
Thanks to its central position on the map, really in the hearth of Tuscany, after spending a few days here you can easily continue your cycling journey to nearby Monteriggioni or Siena, or head east to the popular Chianti region.
Cycling as an experience
My approach to cycling tours reflects the character of the Val d’Elsa itself.
With Asimismo, I work with a limited number of guests, creating tailor-made experiences that are unhurried, discreet, and deeply personal.
An experience based on attention to detail, local knowledge, thoughtful routes, and the freedom to ride without rushing: stopping when the light is right, when a view deserves silence, or when an espresso calls.
Asimismo’s guiding tours are completely bespoke, there are no pre-made routes, because to us it is important to listen to our client’s needs.
Val d’Elsa, through a local lens
There are many ways to ride in Tuscany.
Riding in Val d’Elsa with someone who lives here, rides here daily, and understands its subtleties offers something different.
Choosing to plan your cycling holiday with Asimismo will give you access to places you wouldn’t find on a map, with a rhythm that follows the land rather than an itinerary.
During the years, we have established numerous collaborations and we count on trusted partners working like us in tourism:
many hotels, villas or authentic places like the bio Agriturismo Belmonte Vacanze, a stunning traditional location in Montaione, which is also the starting point of our Gravel Week.
a great selection of bike businesses to rent bikes for those that are not coming with their own.
and many other activities such as wine tasting, helicopter tours, cooking classes and so on.
For me, guiding and photographing these roads is not a job, it is a continuation of a relationship that began long before cycling became my profession. Out there riding, surrounded by this countryside, I constantly find all the inspiration I need in life and the passion for driving this business. I feel privileged to live all of this daily and I am very confident that every of my clients that came here could confirm this.
If you are looking for one of the most authentic cycling experiences in Tuscany, the Val d’Elsa is where I would start.
In case by reading this article some sort of interest sparkled in you, if you would like to be guided by us around this area or if you simply need support planning your cycling holiday in Tuscany, feel free to reach out and discover our full offer, we would love to hear from you.
Included on any guided tour there is always a photographic service. Something unique, for you, to remember these moment forever.
