From Casole d’Elsa toward Monteriggioni

A looped excursion among the sites of ancient battles, fairy realms and gentle landscapes that are impossible to forget. The route runs from Casole d’Elsa to Monteriggioni, the medieval outpost from where Siena defended its borders, so imposing and solid that it earned a mention in Dante’s famous “Divine Comedy.” 
With stretches of dirt road, the ride through the hills is quite easy. These are the sites of the famous battle of Colle di Val d’Elsa, fought between the Sienese and Florentines, when the Guelphs took their revenge on the Ghibellines following the defeat of Montaperti. 

Along the route, expect to encounter parish churches and castles of great interest, as well as to cross the ancient Via Francigena at several points. This pilgrimage road has connected the cities of Canterbury and Rome since the year 1000, crossing the entire length of Tuscany and traversing the landscapes of Valdelsa Valdicecina.

Not to be overlooked is the passage from the Elsa River Park, a slice of paradise where turquoise waters flow, which can be visited along a walk of about 2.5 miles (4 kilometers). Close to urban settlements and a destination for many visitors seeking refreshment, the park is home to undisturbed species of birds and fish that have chosen the Elsa River, in the stretch that “comes to life,” as the locals say. 

In detail, the itinerary starts from Casole d’Elsa, a delightful village perched on a hill, from which we take the road in the direction of the locality Il Merlo, before turning off and coming to Lucciana. Prior to reaching Grazie, a small neighborhood in Colle di Val d’Elsa, you can admire the Abbey of Santa Maria Assunta in Coneo, located along the Via Francigena.

You then reach the Elsa River Park from the road leading to the villages of Boscona and Scarna. The junction with Via Cassia is located at Caduta. From here, you reach the bicycle path that leads from Castellina Scalo to the Colonna di Monteriggioni, a well-known resting place at the foot of the castle, which can be reached from the municipal road leading to the entrance of the village from the centuries-old Porta Fiorentina.

With its 14 towers arranged in a circle like a crown, Monteriggioni exudes a timeless charm. Even Dante Alighieri was impressed, so much so that in Canto XXXI of the Inferno, he compares the towers to the terrible giants stuck in a circle around the well of Malebolge.

The second part of the route entices you with a rather low level of difficulty. Returning to Via Cassia, pedal until you reach the monumental complex of Abbadia a Isola, one of the most evocative pilgrim accommodations along the entire Via Francigena, home to the MAM - Archaeological Museum of Monteriggioni.

Once past Castel Pietraio, you get to Strove, a small village of Lombard origin. From here, turn yet again towards the Elsa River and, after crossing the waterway, proceed to Mensanello, pedaling along an isolated and beautiful paved road.

The surrounding hills provide a pretty backdrop, accompanying you on our journey until framing the village of Casole d’Elsa, located at the top of the hill at the entrance to the SP27 provincial road. Enjoy a gentle climb to the finish line, ready to head out to explore the village. Peppered with sculptures and works of contemporary art, Casole d’Elsa guards its Etruscan soul in the halls of the Civic Museum of Archeology and the Collegiate Church, a treat not to be missed.