Exploring Valdelsa’s Delights on a Weekend Cycling Adventure

If you’re a passionate cyclist and a connoisseur of great food, get ready for an unforgettable weekend dedicated to exploring Valdelsa and its culinary treasures. Prepare for an immersive experience that embraces the traditions and authenticity of this area.

The adventure commences in the picturesque Colle Val d’Elsa, renowned for its expertise in crystal making and its natural gems, including the Elsa River Park, ‘Le Vene’ springs, and the ancient Etruscan Caldane baths. From here, you can also easily travel to other Tuscan locations such as Siena, Volterra and San Gimignano.

Trasqua- bench with panoramic view of Valdelsa

For the night, the advice is to fully immerse yourself in themedieval atmosphere of the upper part of Colle Val d’Elsa. Here, you will have the opportunity to stay in authentic Tuscan homes, such as“La Casa sulla Via Francigena,” a beautiful tower house passionately managed by Simone Demian Turi, who will be your affable host.

Both routes are designed to be affordable for everyone, especially if tackled with comfortable e-bikes. The routes will traverse secondary roads with minimal traffic and picturesque white trails, each approximately 50 km in length. Now, let me guide you through the highlights of this extraordinary journey.

DAY 1: the ring from Colle Val d’Elsa.

We begin our adventure in the heart of Colle Val d’Elsa, the striking Piazza Arnolfo di Cambio, dedicated to the well-known sculptor and architect from Colle in the late 1200s. From here, we will ride south, following the main road towards Grosseto. Upon reaching the hamlet of Gracciano, we will follow the fork leading through the small villages of Ponelle and Scarna, reconnecting with the traditional Via Francigena route.

The next stop will be the charming village of Strove, which will welcome us in a monastic combination of silence and quiet, the main characteristic of rural settlements in the Montagnola Senese area. The church of San Martino and the scenic Castel Pietraio bear witness to the historical significance of this ancient settlement.

Cypresses of Valdelsa

Following that, a gradual descent will lead us to the thousand-year-old district of Abbadia Isola The abbey’s positioning along the Via Francigena rendered it a crucial stop for pilgrimsthroughout the centuries.

We will then continue along roads that cross flat fields, giving us unforgettable colors and scents, until we reach Monteriggioni. A pause to admire the castle and its fortified walls is an absolute must.

The afternoon among the villages and flat roads of Valdelsa

After such exertion, it will be delightful to rejuvenate at the restaurant“La Dama nella Vigna,” will serve us delectable dishes against a unique and stunning backdrop.

We will resume our journey towards Lornano, cycling on a beautiful dirt road surrounded by dense forest, offering a picturesque and scenic passage. Upon reaching the ridge, a panoramic view of the Chianti and Valdelsa hills will greet us, followed by a stretch of the route winding through vineyards and olive groves.

Paurano - panoramic view

We’ll traverse the small village of Rencine, home to a remarkably preserved ancient Romanesque church. A swift descent will guide us back to the plains. After a short stretch on asphalt, we will take the fork to Casale dello Sparviero. Two rows of iconic Tuscan cypress trees will form a stunning corridor guiding us back to an elevated, hilly terrain. The unpaved road that will follow, with the typical up-and-down pattern of this area, will take us to Poggibonsi passing through the small towns of Lecchi and Megognano.


Once in Poggibonsi, we will walk through its historic center, largely rebuilt after the bombings of World War II. If you are interested in finding out more about the city’s history, I recommend visiting the Poggio Imperiale, where you can explore the Archeodrome, the Fonte delle Fate, the Medici Fortress and the nearby Basilica of San Lucchese.

Subsequently, we’ll arrive at the hamlet of Montemorli, where we’ll explore the farm bearing the same name. Here brothers Carlo, Vittorio and Guido Conforti will take us on a tour of one of the oldest wineries in the Siena wine district. We will taste their fine wines, accompanied by typical Tuscan delicacies, all with the view of San Gimignano in the background.

We will resume our route by returning to the plains and following the “green road,” a bicycle path built on the route of the old railway line between Poggibonsi and Colle Val d’Elsa. The route, featuring a level terrain and a compacted surface, will lead us back to the starting point, offering breathtaking views of the valley along the Elsa River.

DAY 2: Discovering the flavors of Valdelsa

Welcome to the second day devoted to exploring traditional Valdelsa flavors. We’ll begin by taking the same route as the previous day, but this time, we’ll continue straight towards the Gracciano traffic circle to reach the Santa Giulia Bridge.

At this point, we’ll take the detour to Scorgiano, an ancient medieval estate. Here, you can admire the Church of Santa Fiora and the Bichi Borghesi Estate, featuring a splendid 17th-century villa, historic stables, and an expansive centuries-old park.

We’ll proceed along the picturesque rolling road towards Pievescola, then head towards the Verniano junction. From there, the journey will continue on the typical Tuscan dirt roads made of dust and gravel.

Badia a Coneo - Abbey with cyclist

We’ll traverse the quaint and enigmatic ancient hamlets of Collalto and Paurano, before returning to the paved road that leads to Casole d’Elsa, renowned as one of the most romantic villages in the Sienese hills. Its historic center is quite picturesque, redolent with works of art by artists from around the world and full of narrow alleys branching throughout. From the height of 420 meters, it will be possible to admire the entire surrounding area: Radicondoli, San Gimignano, La Montagnola Senese, and much more.

After visiting the village, we will pause for lunch at “Il Colombaio” restaurant, run by a DOC Casolese family. Here we will be able to enjoy typical Tuscan dishes prepared with passion by Grazia, the hostess, and relax before returning to cycling.

In the direction of Volterra among vineyards and olive groves

After a good coffee, we will resume in the direction of Volterra, cycling along a wide, scenic and little-used road. This heavenly stretch will lead us to Montemiccioli, a small settlement, dating back to the 14th century. Remnants of the fortified walls, along with the ruins of an impressive tower, can still be found here, situated atop the ridge that divides the territories of Volterra, Casole, and San Gimignano. Legend has it that this tower served as one of the “passaggerie,” where the town of Volterra imposed tolls and collected taxes on goods entering or leaving its territory.

We will return to the present time by taking the road from Montemiccioli to Castel San Gimignano. Before entering the town we will turn right, following the signs for Il Palagio. This beautiful establishment is nestled amidst an expanse of vineyards, where the Zonin family will graciously host us for a tasting of their high-quality wines.

Back to Colle Val d’Elsa

After this rejuvenating break, we will continue cycling toward Colle Val d’Elsa. The route will persist on a dirt surface, leading us into the valley of Poggio ai Colli. Here, you’ll pass through a small gate (remember to close it after passing!) and tackle the uphill climb to Dometaia, home to the Etruscan necropolis of the same name.

Via Francigena

We will proceed through Buliciano until we arrive at a crucial point for those journeying on the Via Francigena: Badia a Coneo. At this location, stood an ancient monastery dating back to the year 1000. Today the Romanesque-Senese style church remains of the abbey.

As we pass Coneo, we reach the conclusion of our tour. Before returning to the starting point, we’ll make a visit to the upper part of Colle Val d’Elsa. Entering through the Bastion and wandering the cobblestone streets will envelop us in an atmosphere with a distinctive medieval flavor. Our final essential stop will be the Bastion, a scenic terrace offering a panoramic view of the entire lower part of the city.

Wishing you a fantastic journey of discovery in Valdelsa and a delightful dining experience!


Text and photos by Enrico Rugi