Grand Tour Valdelsa Valdicecina

The itinerary starts out from the Poggibonsi Railway Station, as the main intermodal point of the Grand Tour. In just a few miles, we reach the settlement of Sant’Appiano followed by the Chapel of San Michele Arcangelo, all that remains of the destroyed fortified city of Semifonte. 

We head along to San Gimignano, a medieval jewel and UNESCO World Heritage Site. Among the towers and alleys, we even discover the contemporary soul of the town, thanks to numerous open-air artworks. 

From the city, the road climbs steadily, offering panoramic vistas of the towers and countryside. Up and up, we reach the Convent of San Vivaldo, the “Jerusalem of Tuscany”.

A descent and subsequent ascent take us to the land of cliffs as we reach Volterra, an Etruscan city known for its alabaster and for the Guarnacci Museum, where the Ombra della Sera—a mysterious votive statue with a longiline form—stands out. The stage is challenging, with stretches of steep gradients rewarded with views of and an immersion into the eternal beauty of Tuscany.

The road between Volterra and Montecatini Val di Cecina is easy, with a single climb leading to the village, where the largest copper mine of 1800s Europe was once found. The Mining Museum (Museo delle Miniere) tells the story of the area’s ancient quarrying vocation, dating back to Etruscan times. From the Belforti Tower, one can admire the mighty fortification of the Rocca Sillana in Pomarance, the Mastio (or, Medici Fortress) in Volterra, and even the sea! 

Continuing on, we come to Pomarance, the geothermal capital of the world, surrounded by geysers, fumaroles and lagoni (geothermal lagoons). The 5-mile (8-kilometer) climb is gentle and even quite pleasant. The town is perfect for an extensive break between nature and culture. Here, history and contemporary art intertwine with tasty culinary traditions. Don’t skip out on tasting the typical sweets of Ricciarelli Pomarancini. If you’d like, a detour to Ponteginori makes it possible to reach the sea in Cecina by train—but this is just an idea and by no means a surrender! 

The stage offers a ride through nature and history, to be interspersed with well-deserved moments of relaxation.

We resume our journey by following the road to Radicondoli, a village surrounded by greenery and nestled in the Cornate and Fosini Nature Reserve. The fatigue of the climb is rewarded by grandiose views. Geothermal phenomena mix with the hilly characteristics of the Sienese territory, as puffs of steam rise far above the green sea of endless forests. 

Before Radicondoli, a detour leads to the hidden villages of Anqua and Belforte.

Continuing toward Casole d’Elsa we reach Mensano, a crescent-shaped medieval village with spectacular views of the Colline Metallifere. Casole d’Elsa, a Bandiera Arancione village, welcomes visitors with its historic center, works of art and the Archaeological and Collegiate Civic Museum.

The road then takes us to Colle di Val d’Elsa, the city of crystal and the “Bohemia of Italy”, uniting history and modernity. In Colle Alta beats the ancient medieval heart, while Colle Bassa invites you on a discovery of Piazza Arnolfo and the Crystal Museum.

We resume our journey by following the road to Radicondoli, a village surrounded by greenery and nestled in the Cornate and Fosini Nature Reserve. The fatigue of the climb is rewarded by grandiose views. Geothermal phenomena mix with the hilly characteristics of the Sienese territory, as puffs of steam rise far above the green sea of endless forests. 

Before Radicondoli, a detour leads to the hidden villages of Anqua and Belforte.

Continuing toward Casole d’Elsa we reach Mensano, a crescent-shaped medieval village with spectacular views of the Colline Metallifere. Casole d’Elsa, a Bandiera Arancione village, welcomes visitors with its historic center, works of art and the Archaeological and Collegiate Civic Museum.

The road then takes us to Colle di Val d’Elsa, the city of crystal and the “Bohemia of Italy”, uniting history and modernity. In Colle Alta beats the ancient medieval heart, while Colle Bassa invites you on a discovery of Piazza Arnolfo and the Crystal Museum.

From Colle di Val d’Elsa begins an easy route that takes us to Monteriggioni, with an initial section characterized by light traffic to be mitigated with a stop in the Elsa River Park. Continuing along the ancient road and pilgrimage route of Via Francigena, we encounter the small villages of Strove and Abbadia a Isola, a monumental complex dating back a thousand years and pilgrim refuge, now home to MaM. Catch your breath here before tackling the climb leading to the Castello di Monteriggioni. Its circular walls are mentioned in the Divine Comedy, when Dante compares the fearsome Giants to the castle’s 14 towers, which you can even climb to enjoy unparalleled views (but no giants!).

The route to Poggibonsi passes through secondary roads and along bicycle paths, offering detours to Castellina Scalo and the Rocca di Staggia, a stone castle with towers that dates back over 1,000 years. In Poggibonsi, we can visit the archaeological area of Poggio Imperiale and the Archeodrome, an open-air museum dedicated to the Early Middle Ages. This is the perfect end to the tour, as you reflect upon the thrills and beauties encountered along the way.