My name is Alessandro, I will be guiding you through the best gravel trails of Tuscany. I will be showing you the landmarks and talking you through about all the historical aspects that made Tuscany the region it is now since early in its history.

I am your “local boy”, I have grown up here. With me you will get to see this territory with the eyes of a native. We will ride along the most picturesque roads and appreciate the scenery as you have never done.

The best gravel experience in Europe

We will cross and admire the beautiness of medieval towns standing on hilltops and tackle the best white dusty roads often surrounded by lines of cypresses and vineyards.

Starting from Iano, located in the southern side of Montaione, we will spend a week together riding every day through a different part of the Tuscan countryside along the legendary Strade Bianche, twisty dusty roads connecting villages and colonial houses in between rolling hills.

Day 1: Welcome to Tuscany

[35 km + 800m] with 80% paved and 20% dirt


On arrival day, after settling in in the morning, we will enjoy an afternoon riding a short loop, discovering the ghost town of Toiano: you will already begin to discover how beautiful and special Tuscany is by bike. We will have time to get acquainted with each other, and each participant will receive a welcome-gift.

Day 2: The medieval town of Boccaccio

[74 km + 1600m] with 75% paved and 25 % dirt


Gravel ride towards the historical old town of Certaldo, homeland of the Italian novel author of the Decameron. A place full of history and breathtaking landscapes. The orange from the old towers, the green hills and the blue sky is a combination not to miss.

Day 3: The Theatre of Silence

[78 km + 1160m] with 61% paved and 39% dirt


Gravel ride around Terricciola and Lajatico in the province of Pisa: we will be visiting the “Teatro del Silenzio”, the Theater of Silence, an original artitechtonical piece of art blending the landscape with culture. Singers such as Andrea Bocceli sang here. We will be discovering it by bike.

Day 4: Keep it local

[56 km + 1110m] with 41% paved and 59% gravel


After two solid days of riding we will take it a little bit easier. We will remain fairly local, around the area of the Agriturismo riding the nearby trails and admiring the famous Calanchi. In Tuscany, local never means boring.

Day 5: The Etruscan route

[70 km + 1300m] with 68% paved and 32% dirt


On day 5 we will be riding around the beautiful Volterra. This land is famous for its pilgrims and Etruscan settlements, and for its “Balze & Calanchi”, a geological phenomenon forming an erosive/deserted area where there were higher mountains in the past. Riding through these roads will be a lifetime experience.

Day 6: The Town of Fine Towers

[76km + 1650m] with 57% paved and 43% dirt


Our last day riding will take us to visit one of the most iconic places in Tuscany and the trails nearby. This medieval town, San Gimignano, is famous for its very iconic and tall towers. From the top, the view is postcard-like: Tuscany at its best.

Day 7: Arrivederci

Even the nicest things will eventually end. Until next time!

After a good breakfast we will help you pack your bike or take it back to the rental. There will be a time to share about the experience with the group, and we will be handing to each of the participants the photos from the week: memories to carry forever, with the hope of seeing you again next time.

Technical information

In case you bring your own gravel bike and are not renting one a minimum of 700×34 tyres is required. Best compromise in terms of comfort and grip on these trails can be found with 700×40 tyres.

We recommend you riding a front chainring not bigger than 42 teeth. Optimal gear ratio can be 38/42 front with 11-40  at the back.

Mtb are also welcomed but do not expect very technical trails. All the roads we will do are suitable for gravel bikes.

Get in Touch

If you want to discuss it further, if you don’t see a date on the calendar that suit you or have any questions, feel free to get in touch via the dedicated form or via email.

For this week we are partnering up with Belmonte Vacanze situated in Iano. This resort is, what we can call, a very Tuscan authentic bio agritourismo managed by the Lotti family inside a private park property of 200 hectares. 

Your staying…

Located in between the three stunning towns of Volterra, San Gimignano and Montaione, Belmonte Vacanze in Iano is the best starting point for every day tour, for its gorgeous and strategic position.

No matter the direction we’ll take, we’ll find scenic and breathtaking trails. 

This farmhouse and holiday home immersed on the Tuscan hills is our pick to make your riding week an unforgettable experience.

At the end of the day, you’ll be able to enjoy the facilities this structure has to offer you.


From a  tennis court to an Equestrian center, you’ll find yourself living a truly Tuscan experience.

When it is time to relax, the panoramic swimming pool of 350 mq with jacuzzi will be waiting for you, offering its spectacular view.

The accommodation is in typical flats furnished in Tuscan style with all the comforts. Free WIFI, air conditioning/heating with remote control, dishwasher and balcony or terrace.

It also has its own restaurant, where you will be able to enjoy a tasty breakfast in the morning and great dinners prepared by the Lotti family with organic products, cultivated in the surrounding area, all while enjoying typical Tuscan dishes made with traditional recipes.