Route that allows you to face a medium-long walk during the day with only the final stretch after sunset.

From Siena, after crossing the center you arrive at Porta Romana and you go down towards south-east on asphalt and then on a dirt road up to the Certosa di Maggiano (km 2.17) and continue slightly downhill until the area of Ruffolo where you pass over the SS 223 of Paganico (km 4.37).

Continue along the Certosa road and pass a traffic circle (km 6.9). At km 8.6 you turn right on the road of Borgo Vecchio and you’re near the industrial area of Siena, you cross the Cassia near the hill Malamerenda (km 9.7) and here you take the path originally traced by the Tuscany Region that leads to the dirt road of Radi; you follow it for a while and then you turn left (farm Belvedere km 12) going slightly up the hill through a succession of farms and cultivated fields. On the left there is the tower of tomatoes, a cylindrical concrete structure 50 meters high, built in the 60’s for the freeze-drying of tomatoes and never entered into operation. The tower is visible from miles away and has become an element of the landscape.

We approach Ponte a Tressa (km 15) until we reach the Grancia di Cuna at km 16.8. The Grancia is an ancient fortified granary owned by Santa Maria della Scala, currently under renovation. It remains on the left of the route that continues in a southerly direction.

After the town of Monteroni (km 18.4), the route continues halfway up the hill among hills cultivated with wheat, passes the Poggio del Cipressino at km 19.7 and arrives in Quinciano (km 21.9). After Quinciano, you have to ride along the provincial road 34 for a short stretch and then you have to cross it to get onto a dirt road (km 22.5) that runs along the railway line, first on the right and then on the left. It goes through farms and chianina cattle breeding and arrives in Ponte d’Arbia (km 27.6).

You cross the Arbia river on the new wooden pedestrian bridge (km 28) and then you cross the Cassia road. After a few ups and downs (between the areas of Serravalle and Poggiarello) you’ll reach the crest (km 30.9) with the Arbia valley (and the Cassia) on the right and, on the left, beyond the Ombrone river, beautiful views of the Crete area (up to the abbey of Monte Oliveto Maggiore).

When you reach the cemetery of Buonconvento, go downhill (km 32.1) and, after a stretch along the edge of the Cassia, crossing the Ombrone just before its confluence with the Arbia, you’ll skirt the town, entering through the northern gate and following the central road. It is advisable to take advantage of the refreshments with hot dishes before embarking on the second part of the route.

We cross the Cassia again and we go slightly upstream crossing the area of the sports facilities and craft activities. You have to go down along a concrete ramp and at km 35.1 you have to cross again the Cassia road for a few meters and at the fork you have to take the provincial road on the right towards Montalcino, walking on a path along the road (km 35.5). We leave it at a point where the Ombrone river, which is on our right, makes a sharp U-turn and we ford a small ditch that acts as a border between Buonconvento and Montalcino (Serlate torrent 36.9 km).

We continue for about one hundred meters at the edge of the road and then we turn left (km 37.2) and we begin a long stretch of dirt road (almost 10 km) in the middle of the Brunello hills (among vineyards and cultivated fields) passing by the farms Castello Tricerchi, Altesino (km 38.5), Casella and when we reach the church of San Sebastiano we turn left at the farm Collodini (km 41.3).

You have to pass the Viti Farm, the Incontro Community and the Desertino Farm (44.5 km) until you reach Torrenieri (hamlet of Montalcino) at km 46.2. After leaving Torrenieri begins a stretch of a couple of km in which you have to ride on a path along the road (in some point directly on the road). Keep right at the crossroads at km 49.1 until you leave the paved road and abruptly turn right at km 50.7 in correspondence of a large gas station.

We pass under the Cassia road (km 51) and the dirt road continues having on both sides farms with stretches of woodland until you reach, with a small final stretch (km 54), San Quirico d’Orcia. We cross the town rich in monuments and here ends, in Piazza del Comune (km 54.3), the route Siena San Quirico.