Voyage into the intimacy of the land of Siena From Poggibonsi to San Galgano: 92 KM.

Here is the real voyage to discover a land less known in the province of Siena. This route is mainly of a north/south orientation which takes you into a world of greenery, where a thick woods alternate with the fascination of the Metallifere hills and the vistas of the western part of the province of Siena and the wild Maremma. Pristine nature and medieval “Borgos” follow one another in this part of Tuscany which is untamed and conserves its secrets of an authentic land.

The trip begins in Poggibonsi, an antique borgo, which despite its modern aspects, offers the visitor an historic center of great valore. It lies where the rivers Staggia and Elsa join together. There are several reasons to visit this borgo, the “Collegiata, the 13th century church of San Lorenzo, the Palazzo Pretorio, the church of San Lucchese. From Poggibonsi it is easy to reach San Gimignano, the city of the towers. Here you’ll find yourself in one of the most visited towns in Italy which naturally needs no particular introduction. Our suggestion is to enjoy this town when its streets and alleys aren’t being invaded by tourists, in other words, the early morning or just before sundown. From an urbanistic and architectural point of view this town is a doorway into the atmosphere of the Florentine Republic of the 13th century. Of the 72 original towers only 15 are still standing, they look out over the maze of tiny streets that criss-cross San Gimignano from the Piazza of the Duomo and the Piazza of the Cisterna. Our trip continues along the route of the Vernaccia, a special wine typical of the zone, proud of its heritage (first D.O.C. wine in Italy and now a D.O.C.G.) which proposes itself in contrast with the other, great, famous and rich reds of Tuscany.


At Castel San Gimignano you will turn right for just a bit on S.S. 68 (direction Volterra) and then, left towards Casole d’Elsa. From here the voyage into the most intimate and secret part of Tuscany begins, entering fully into the Val d’Elsa. Soon you’ll come to Casole d’Elsa, a fortified outpost of the Republic of Siena. The outer walls of the city conserve on the eastern side two circular towers, the Collegiata of Santa Maria Assunta (1161 AD) and the Palazzo Pretorio. Together with the castle (Rocca) from the 13th century, these structures constitute the stone axis upon which the historical memory of this ancient borgo stands, giving peace and tranquillity today, especially to the surrounding countryside. Decidedly up and down, one of the most beautiful roads in the area will bring you an antique borgo-castle called Mensano, from where the rest of Tuscany seems far away. Here it’s easy to perceive the human dimensions of the zone. From Mensano you’ll continue on, following directions for Radicondoli. After 7 KM. you will come to Localita’ Casone where you’ll bare right, arriving at Radicondoli.

Welcome to an unforgettable look out. Proceeding through the village on the main street you will come to a small piazza with a bench on your right, towards the end of the village. This is the ideal spot from where you can let your gaze wonder over the undulating hills of the land of Siena. A spectacle you won’t want to miss.

Retracing out steps to Loc. Casone, you’ll go right and at the next intersection, right again, passing for Belforte and Montingegnoli. These are two castles far from the main roads and despite their small size they are of rich architectural and urbanistic heritage. From Montingegnoli you will take the road for Montalcinello and then, after, for Chiusdino, entering into the land of the Val di Merse. Now we are in a boundary area, it’s here that the land of Siena looks out at the Maremma. In the borgo of Chiusdino you will find the church of San Martino, referred to as (outside the walls), the Parrocchia (parish) next to the birthplace of San Galgano and the church of the Compagnia Cistercnese di San Galgano with an interesting bas-relief (1466 AD) which shows San Galgano thrusting his sword into the stone. It’s here in the commune of Chisudino that the Abbacy Cistercian of San Galgano is to be found as well as the chapel of Monte Siepi, the final objective of our voyage. The breath taking view of the roof-less cathedral and its sky ceiling is your reward.

Where to stay in Poggibonsi

There are numerous high quality hotels, villas, apartments and agriturismi (Farm stays) available, check them out and make a reservation here.