The hills of Valdelsa

Rolling hills covered in rows of wine, dotted with historic villages alternating with wild woods and deep gorges, which are crossed by streams and thermal waters:  the Valdelsa region has a charming hilly landscape varied and never tires. 

If the Strada del vino di Montespertoli (Wine Road) has always been popular with bicycle enthusiasts and enjoyable all year round, the town of Castelfiorentino, on the other hand, has other unique routes to offer, such as the Giracastello, consisting of two cycling trails that start from the village and follow the Elsa stream. These trails will let you discover the area while touching historical places, such as the Tabernacle of the Madonna della Tosse, the Villa di Cambiano and the Villa Tinti where Giuseppe Garibaldi, Italian patriot and leader of the Risorgimento, stayed overnight. 

For those who love hiking, Montespertoli, Certaldo and Gambassi Terme offer a wide range of options. The via di Castiglioni, in Montespertoli, is an educational trail that starts from the Castle of Montegufoni and goes up to Ginestra Fiorentina. Along the way, you will find stop-off areas featuring information about the territory and its landscape. The interesting Water routes are four easy trails in the area around Montespertoli: the Botinaccio, which leads to the Sanctuary of Santa Maria della Pace; the collina del Pino (Pino hill), which connects San Michele a Polvereto to the village of Pino; Montalbino and Montegufoni, which leads from the castle to the Church of San Lorenzo. 

Between Montelupo Fiorentino and Montespertoli, in the area of San Vito, you can follow the ring route bosco di Camaioni, along the way it is possible to admire the Church of San Michele a Luciano, the astronomical observatory “Beppe Forti” and the remains of an ancient medieval fortress, today an archaeological excavation site. 

Three different itineraries start from the imposing fourteenth-century walls of the historic center of Certaldo, birthplace of Boccaccio, enabling you to explore the surroundings of the historic village. The trails, which offer unique views of Certaldo and the surrounding hills, are accessible to everyone but they are not marked, we therefore suggest you to bring a map with you. 

Not far from Certaldo, the woods of Gambassi Terme are the ideal place for outdoor activities. This small town is one of the stages along the Via Francigena and is located at the junction with the Via Volterrana, the ancient salt road that in the Middle Ages connected Volterra to Florence. A network of hiking trails of varying difficulty, called I Casciani, winds all around the village.
The ‘I Bollori’ trail, (which derives its name from the nearby 23°C hypothermal spring), is one of the most remarkable routes, since it allows you to explore an area with a high concentration of thermal waters.
The Grottoes of Maurizio trail is a very impressive walk through the woods up to a gorge carved by the Casciani stream.

Lastly, the Vecchio Acquedotto (Old Aqueduct) trail goes up the stream towards Poggio alla Forra where you can find the remains of the ancient aqueduct of Gambassi and Montaione. You can enjoy all these trails on your own, but some stretches will require experienced hiker skills.
If you wish, it is possible to rely on environmental guides.