Photo © / Annavee
3 Days' Hiking in the Chianti
A sea of hills between Florence and Siena
39 km
3 giorni

The Chianti is a beautiful range of hills with a history of hundreds of years and long disputes, a place of fortified hamlets that stand out in the middle of woods and farm fields, and ideal for a trip to discover the food and wine traditions of Tuscany. The varieties of Chianti Classico DOCG, with their unmistakable profiles lending the table a splash of red nectar colour, are without doubt the local jewel in the crown.

The Chianti uplands are high thanks to a range of hills, in which Monte San Michele, the tallest peak, reaches almost to 900 metres, and are irrigated by five rivers and numerous little streams.

Travelling through this landscape is a true sight for sore eyes: on the small, provincial farm roads the hills never run out, always giving you a varied, magical view. These are the panoramas of Tuscany that you dream of, studded with little villages wrapped in the relaxed atmosphere of central Italy, where every break you take in bars and trattorias yields interesting and spontaneous encounters, as befits Tuscan hospitality. There is Greve in Chianti, which with its Wine Museum stands as gate to the region, Castellina and its archaeological museum, Radda and Gaiole nestling in the hills, the fortified town of Barberino Tavarnelle, San Casciano Val di Pesa, where Machiavelli lived. And then an endless series of villages and hamlets, little stone bubbles enclosed by walls and dotted with medieval churches, parish churches.

We therefore dive into the heart of the old Grand Duchy, distancing ourselves from the traffic and driving down the innumerable little white roads which - like an unending lattice - are carved into this mythical landscape. Before us are only the silence of the woods and the chatter of the birds, who every so often come to rest between the precious vines. The point of departure of each excursion must be reached by car.

first day
The Cintoia Circuit
The Chianti
The Chianti - Credit: / Marco Saracco

Our route begins at Cintoia, a town about twenty kilometres south of Florence, between hills well distant of the tourist crowds that swarm the Tuscan capital. Following the outline of an ancient Etruscan road, we head into the woods of the Chianti from Castello di Mugnana, an imposing fortress built upon a rock in the fourteenth century. Taking an ascent up path no.18, we pass into a thick wood of pines and holly oaks which gradually, as we climb, give way to chestnut trees. We stick to the ridge until the farmhouse of Casa al Monte, then descend towards La Panca.

From here the path follows the ancient Etruscan road that connected Volterra to Fiesole. When path no.18 deviates to the left, there is the possibility of visiting the Abbey of San Cassiano a Montescalari (from the outside), which leads onto the main road: the old religious building, of medieval origin, was fortified around the year 1000 and enjoyed its greatest prosperity at the beginning of the fourteenth century. Returning to path 18, we start descending towards the castle of Cintoia Alta, after which the path comes close to an old mill. From here we dive again into the woods on a path that hides some traces of Roman and medieval paving. This woodland stretch winds its way towards a river, which is crossed by small stone bridges in many places up to Castello di Sezzate, an old twelfth-century complex which in medieval times had a rich marketplace. We go down among the olive trees and ascend again towards Castello di Mugnana, only a few metres from where we started.

second day
The Radda Circuit
The Chianti
The Chianti - Credit: / Diego Mariottini

On the second day of hiking we turn towards the Sienese Chianti for a panoramic itinerary of ancient towns and architectural works of great histori value. We start from Radda, an old medieval town that was the headquarters of the Lega del Chianti in the 1200s. The tradition of wine began in these hills over two thousand years ago, when the precious vineyards were already being cultivated during the Etruscans period.

After admiring the walls and the elegant palazzo del Podestà, we depart from the old mill on a dirt track that leads into a climb. We arrive at Poggio di Montemaggio and proceed on the path towards Castelvecchi. This little settlement is a centre of wine production, and today a place of hospitality; it is where millennia-old vineyards guard the tradition of Chianti Classico DOCG, and also of pinot, prosecco, grappa and olive oil.

We continue on the white roads that lead to Volpaia and Villa al Monte, and on the way find the church of the Madonna del Fossato, a little eighteenth-century chapel hidden behind the branches and encircled by cypresses. Built to house a painting of the Madonna and Child, it is a place of real mystery, should you choose to pause there. We then reach the ancient fortified hamlet of Volpaia, another historic contributor to the production of Chianti Classico.

Having visited the village, which unlike many others of its kind offers a structure both medieval and intact, we begin the climb towards the Parish Church of Santa Maria Novella, an ancient Romanesque church from the twelfth century, after which it will be easy to reach the starting point by following the white roads that flank the famous vines.

third day
The Lecchi Circuit: the heart of the Chianti
The Chianti
The Chianti - Credit: / Antonio Truzzi

We move a few kilometres, taking Lecchi as the starting point of another route that brings the historical and natural treats of the Chianti region into full view. From this hamlet we descend towards the Osteria della Passera and soon arrive at the Rocca di Tornano, an old quadrangular fortress which dates to around the year 1000 and today functions as a relais hotel. We walk among small farms that neighbour the famous villas, gradually finding ourselves in woods, until we emerge at the farm of Castello di Cacchiano. From here we can see the most iconic sights of the Chianti, from the hills to - on the clearest days - the towers of Siena. We then head towards Monticello and continue to descend to a little stream, which we follow to Le Macie. We hit tarmac again and stay on it until San Sano, a small hamlet that in the past was probably strengthened inside by a fortress, and today is one of the better-preserved hamlets in the region, with its stone construction. We climb again through the greenery and reach a farm track that will take us back to Lecchi, but not before passing by the castle of Monteluco. A fortress built in 1100 under the government of Siena, it became Florentine and remained contested between the two powers over the centuries. Having seen this impressive structure, we are soon back to where we started at Lecchi.