Arrival is scheduled for the morning at an agriturismo (farm stay) in San Gimignano, your base for every day of the trip. The town dominates the surrounding countryside and can be seen from miles away thanks to the skyline of its 14 medieval towers. The landscape around the village is a neat patchwork of Vernaccia vineyards, olive groves and rows of cypress trees following the curves of the land: the quintessential Tuscan landscape.

After check-in, the route heads north along a gravel stretch of the Via Francigena. The first stop is the Pieve di Cellole, an ancient Romanesque church sheltered by a cypress grove in a quiet, secluded spot. The ride continues towards Gambassi Terme, where the vegetation becomes thicker and more wooded, before opening up on the descent into the Val d’Elsa plain.

From here the road climbs again towards Certaldo Alto, a hilltop village built entirely of red brick, a reminder of the area’s long tradition of working local clay. Leaving Certaldo, the route winds through the hills of Petrognano, covered in farmland and vineyards. Suddenly, through the trees, the Dome of San Donnino comes into view: a 1:8 scale replica of Brunelleschi’s Dome, standing on the hill where the ancient town of Semifonte, Florence’s historic rival, once stood. The ride back to San Gimignano follows a scenic ridge road, with the town’s towers always on the horizon.

Ride back to San Gimignano

This stage has the toughest elevation gain and shows a striking change of scenery. After leaving San Gimignano and passing the small village of Castel San Gimignano, the gentle wooded hills give way to a starker, barer landscape. The road climbs towards Volterra past the calanchi and the Balze, dramatic chasms and natural erosions in the clay soil that expose layers of grey and golden earth.

At 531 metres above sea level you enter Volterra, an Etruscan city perched on the rock. From the centre and Piazza dei Priori, a sweeping view stretches over the whole Val di Cecina all the way to the sea. Here you’ll have plenty of time to enjoy the city and its treasures. After a well-deserved rest, you set off on the return journey, descending along the trails of the Berignone Forest Nature Reserve, surrounded by dense Mediterranean scrub and holm oak woods, before climbing back up to base.

Ride back to San Gimignano

On the final day we pass through Colle di Val d’Elsa, a town known for its crystal craftsmanship and divided into a historic upper town and an industrial lower town, and the Elsa River Park (SentierElsa): the ride follows the riverbank, sheltered by thick vegetation, where the water turns turquoise and forms small cascades.

We’ll see Le Caldane, ancient pools of warm thermal water dating back to Roman times, and, following the Francigena, ride through Strove and the Abbadia a Isola plain until the hill of Monteriggioni comes into view, with its almost perfectly circular walls punctuated by 14 rectangular towers. Here too you can stop to wander the streets and enjoy a well-deserved rest.

Ride back to San Gimignano before nightfall, bike return (if applicable) and check-out