Cycle paths and trekking. Via Barlettaia Pienza-Montepulciano

From the centre of Pienza, head north, following the paved SS146 state road towards San Quirico d’Orcia. After about 1 km, at the Pietrafitta junction, turn right into the SP71 provincial road in the direction of Trequanda and San Giovanni d’Asso.

The road descends, running alongside fields and woods, until it crosses a small bridge over the Toma Torrent.
Just after the bridge, turn right, towards the San Polo dairy, leaving the paved road to follow a very quiet unpaved road. Proceed for a few kilometres, alongside the woods and Borgo Sant’Ambrogio, until you come to the junction for Le Regge, where you turn left.
This unpaved road leads onto the SP15 provincial road, where you turn right

From the centre of Pienza, head north, following the paved SS146 state road towards San Quirico d’Orcia. After about 1 km, at the Pietrafitta junction, turn right into the SP71 provincial road in the direction of Trequanda and San Giovanni d’Asso. The road descends, running alongside fields and woods, until it crosses a small bridge over the Toma Torrent. Just after the bridge, turn right, towards the San Polo dairy, leaving the paved road to follow a very quiet unpaved road. Proceed for a few kilometres, alongside the woods and Borgo Sant’Ambrogio, until you come to the junction for Le Regge, where you turn left. This unpaved road leads onto the SP15 provincial road, where you turn right.

After about 3 kilometres, turn left and head towards Lupaia. This is a picturesque unpaved road that crosses the Nobile vineyards, leading to Montepulciano from the Church of San Biagio, its main architectural jewel, which is well worth a visit.

The construction of the so-called Temple of San Biagio began in 1518, based on a design by architect Antonio da San Gallo the Elder, when Montepulciano was part of the Florentine Republic. This is where Agnolo Ambrogini, known as Poliziano, was born. He was a humanist poet at the court of Lorenzo the Magnificent and a tutor to his sons, including Giovanni, who later became Pope Leo X and chose to grant privileges to Montepulciano to honour his former teacher. This central-plan church features a harmonious combination of geometric forms. The stone is calcareous tufa from the quarries of the nearby hamlet of Sant’Albino. Beyond the lawn, stands the rectory with a well in front of it, both designed by Sangallo. A steep road climbs up alongside the rectory, leading to the upper and oldest part of Montepulciano, entering the walls through the Arco del Paolino. Further up, you will come to Piazza Grande, which is 600 metres above sea level. Overlooking the square, you will see the 17th-century cathedral with its unfinished façade, the town hall, designed in the early 15th century by Florentine architect Michelozzo, and Palazzo del Capitano. In front of this building is the beautiful Pozzo dei Grifi e dei Leoni (Well of Griffins and Lions), symbols of Etruscan Montepulciano and Florence respectively, also emphasised by the Medici coat of arms. Completing the square are the elegant Nobili Tarugi and Contucci private palaces, both attributed to Sangallo.  Behind the cathedral block stands the Fortress, surrounded by a public garden.

From the Fortress, go down towards the SS146 state road and carry on for a couple of kilometres towards Chianciano Terme. At the Villa Bianca junction, turn right into the Via della Montagna SP88 provincial road in the direction of Monticchiello. At a certain point, the Via della Montagna splits off from the SP88. The first branch leads to La Foce, where, on certain days of the week, you can visit the splendid gardens. The second leads to Monticchiello, culminating in picturesque hairpin bends lined with cypress trees.

After visiting Monticchiello, go back to Pienza along the unpaved road that starts with the Via 6 Aprile and runs alongside the Casa al Piano farm.

Temple of San Biagio in Montepulciano, Bosco di Poggiano, Monticchiello, Casa al Piano, Pienza

Duration: 3-5 hours, depending on alternative routes and stops.

The hike begins at the Temple of San Biagio, a 16th-century Florentine architectural jewel designed by Antonio da Sangallo the Elder, built as a votive offering of popular devotion where an image of the Virgin Mary performed miracles.
From here, take Via della Peschiera, a downhill stretch, which then becomes Via dell’Aiola and runs alongside the Nobile di Montepulciano vineyards.
Once you are on the SS146 state road, continue right for a short distance until you come to the junction for Poggiano, on the left.
The road begins to climb, until you reach the Via del Termine on the left.

An alternative route specifically for garden lovers: from San Biagio, take Viale della Rimembranza, lined with cypress trees planted in memory of the soldiers of Montepulciano who died in the First World War. Once you are on the SS146 state road, turn right and, after the petrol station, turn left into Via San Bartolomeo.

For lovers of contemporary gardens, we recommend a visit to the captivating Villa Trecci Park, a vast private eco-sustainable site divided into several themed areas, including a rose garden, a wood, a pond and flowerbeds dedicated to different flower species, all sharing a water-saving system and panoramic views.

Resuming your journey, proceed towards Monticchiello, passing alongside the Terre di Nano Farm.

The historic centre of Monticchiello, a bastion of the eastern Val d’Orcia area, can be entered through the medieval Porta Sant’Agata.

A stop in the village is a must, where you can visit the Church of Santi Leonardo e Cristoforo and walk uphill to the castle keep.

To return to Pienza, we recommend the quieter unpaved alternative route that starts from Via 6 Aprile and passes alongside the Casa al Piano and Lucignanello farms, before climbing uphill to the apse of Pienza Cathedral with a significant elevation gain.