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Photo ©Shutterstock.com / Ondrej Prosicky
A journey through vineyards, badlands and picturesque little towns, seen from the Tuscan hilltops

Four Days of Trekking: Discover the Grande Anello of Siena

The Siena territory: a kaleidoscope of varying, sublime landscapes, enclosed in a fold of land around a city recognised as a UNESCO World Heritage Site. To the north, the Chiantihills, known throughout the world for their endless strings of vineyards and villages, at their most beautiful in the autumn when they turn green, yellow, red and brown. To the south-east, the Crete Senesi, themselves a UNESCO World Heritage Site, a realm of badlands and clay that was known in the Middle Ages as the 'Desert of Accona,' thanks to its yellow aspect in summer, its lunar-like appearance in winter. 

The Montagnolaarea to the north-west is less famous, but no less impressive for it. At the gates of the capital city, hiding under its chalky soil, are more than eighty karst caves. On the surface, meanwhile, you find woods of holly oak, where the precious yellow marblethat was used to build the Florence Cathedraland that of Orvieto is mined. Turning to Montemaggio, the highest point of the Sienese Montagnola, we find the beautiful town of Monteriggioniwith its walls which, as Dante noted in the Divine Comedy, encircle it completely.

The Grande Anello (Great Circle) of Siena includes these three areas, full of charm and variety: a journey of seventy kilometres to divide into four stages, along back roads and little dirt paths. You will see places famous for their awe-inspiring positions and hidden corners, rural religious buildings, parish churches and charterhouses, ghost villages, cypress-lined boulevards and small towns where you can restore yourself over a nice glass of something. Sienese Chianti, obviously!


From Isola d'Arbia to Ponte allo Spino

Our journey begins in Isola d'Arbia, a hamlet of Siena situated on the ancient via Cassia. Crossing the Tressa stream and turning towards Podere Nuovo, we suddenly dive into a network of white country roads. We follow the red and white signposts along the dirt tracks for Radi and Poggio ai Frati, in a pleasant climb that finishes on a panoramic terrace. Slanting cypresses line the roads. Heading towards San Rocco, you skirt the Church of San Pietro, after which you arrive in Linari.

Dominating the little zone is an ancient 13th-century monastery which was converted into a country residence during the Renaissance and later transformed into the resort that it is today. Still adhering to the red and white signs, plus additional signage put up by the province, you follow the road for the Pian dei Mori town. Walking alongside the Serpenna stream, we reach our first destination: Ponte allo Spino, where it's worth visiting the ancient Parish Church of San Giovanni Battista

With its warm colours, the church represents one of the most precious examples of Romanesque religious architecture in the whole province. Inside, three high naves are decorated by columns with beautifully made, exquisitely preserved capitals. Next to the church is the little courtyard and palace that hosted the Sienese bishops during the summer months.

second day

From Ponte allo Spino to Badesse

We start the next morning in Ponte allo Spino, heading for Toiano. We reach a little town which served as an outpost of the Republic of Siena, dominated by the 'Palazzaccio', the town’s ancient castle. Having walked down the main street and past a small, Neoclassical church, we head into the woods along Path CAI 113, arriving at Colle dei Mandorli

The postcard views continue unabated, as we glimpse the Villa of Montecagnano and then end up at Santa Colomba. Majestic and imposing, this Renaissance residence which rises from the town centre was built between the end of the 15th and the beginning of the 16th centuries on the ruins of an old medieval castle. Proceeding towards Celsa we come to a crossroads, leading on the right to the 12th-century Hermitage of San Leonardo al Lago, which you can visit with a detour of roughly an hour.

Rejoining Path 113 we reach Fungaia, after which we delve into the woods along Path 106 until we get to Pian del Lago. Climbing again on a wider track we come to Podere Caggio, where we can catch a fantastic view with Monte Amiata in the background. Linking up with Path CAI 104, we arrive at Castello la Chiocciola(Snail Castle), a Sienese outpost in the municipality of Monteriggioni. This site, inhabited since the Paleolithic era, owes its name to its great cylindrical tower and the spiralling staircase within. Going beyond the castle, you proceed towards the small farm of Cerbaia, from which you can gaze at the fortified outline of Monteriggioni. We emerge from the Staggia hamlet and eventually arrive at Badesse, where we spend the night.

third day

From Badesse to Pieve a Bozzone

We resume the road for Miniera, soon finding ourselves in the town of Santo Stefano. Continuously climbing up and down, we head towards La Ripa and then Poggio Teo, a typical hill where cypresses alternate with pines; then further on, among brief stretches of asphalt and dirt track, we arrive at Cellole. On the left, a view of the PontignanoCharterhouse appears before us, a large monastic complex constructed in the 14th century, dominated by a church dedicated to St Peter and enhanced by the colonnaded cloister inside. Following the road, we arrive at the Villa of Monaciano, the garden of which you can visit by asking at reception, then continue towards the castle in Monteliscai.

We are almost at Pieve a Bozzone, our destination of the day. Before our well-deserved rest, however, we move to a beautiful spot overlooking the little Church of San Giovanni Battista, built in the 12th century and restored in the 19th, hidden surrounded by green vegetation.

fourth day

From Pieve a Bozzone to Isola d'Arbia

We get back on the road that leads to Vico d'Arbia. When we come to a crossroads, we can turn left for a brief deviation of two kilometres which takes us to the Villa di Montechiaro, a private estate which hides a wonderful garden in a panoramic vantage point.

Returning to the main road, we cross Vico d'Arbiawith its graceful little church. The route continues along the Arbia Valley, rising again up to the old estate of Presciano. The town, which today lies half-abandoned in peaceful silence, used to be a little dwelling enclosed by clay slopes and little woods. Once a small castle, it was reduced to a village and became a place of legends and superstitions.

We go on until the abandoned farmhouses of Bandita and San Giovannone: here begins one of the most amazing stretches of the famous Crete Senesi, an area celebrated throughout the world for its breathtaking landscapes, sculpted into the form of badlands and 'biancane,' clear grey earth formations characteristic of the area. Keeping to the road for about two kilometres until the Salteano farm, we will eventually arrive at Isola d'Arbia, the starting point of our four-day journey.

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