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Montepulciano – Historic Centre of Pienza loop from Montepulciano

Montepulciano – Historic Centre of Pienza loop from Montepulciano

Moderate

4.9

(17)

408

riders

Montepulciano – Historic Centre of Pienza loop from Montepulciano

02:43

56.1km

770m

Road cycling

Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride. The starting point of the route is right next to a parking lot.

Last updated: June 19, 2026

Tips

The surface along some of this route may not be suitable

Some segments of your route comprise a surface that may not be suitable for your chosen sport.

After 0 m for 68 m

After 847 m for 251 m

Waypoints

Start point

Parking

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612 m

Church of St. Agnes

Highlight • Religious Site

Baroque and neo-Romanesque style church.
It was built in 1306 by the abbess of Poliziana Agnese. At the end of the seventeenth century it was radically renovated.

Translated by Google •

Tip by

1.01 km

Beautiful medieval village to visit. From the view of the vineyards to that of the Val d'Orcia, there is no shortage of views, not to mention the streets and alleys within the city walls. Unmissable Piazza Grande.

Translated by Google •

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2.83 km

Church of San Biagio

Highlight • Religious Site

Walking along the two parallel rows of cypresses it is possible to slowly glimpse the foreshortening of the bell tower that stands out high in the sky. And it seems …

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Tip by

11.9 km

Massaini Castle

Highlight • Castle

Among vineyards, olive groves and medicinal plants, stands Palazzo Massaini, a place where nature, tradition, Tuscan food and wine merge.
Source: palazzomassaini.com

Translated by Google •

Tip by

21.8 km

View of Val d'Orcia

Highlight • Viewpoint

24.1 km

Historic center of San Quirico d'Orcia

Highlight • Historical Site

San Quirico d'Orcia is one of the most historic and beautiful centers in the entire Val d'Orcia. Its history is thousands of years old and the center of San Quirico …

Translated by Google •

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40.0 km

Pienza, City of Pius II

Highlight • Settlement

41.8 km

Historic Centre of Pienza

Highlight • Historical Site

Pienza is a small jewel of the Val d'Orcia, known as the city of Pope Pius II, aka Enea Silvio Piccolomini, who was born here in 1405. Pius II, once …

Translated by Google •

Tip by

56.1 km

End point

Parking

Way Types & Surfaces

Way Types

34.9 km

18.7 km

2.62 km

< 100 m

Surfaces

54.8 km

775 m

540 m

< 100 m

Elevation

Nothing selected – click and drag below to see the stats for a specific part of the route.

Highest point (550 m)

Lowest point (250 m)

Weather

Thursday 16 July

39°C

21°C

0 %

Additional weather tips

Max wind speed: 18.0 km/h

to get more detailed weather forecasts along your route

Comments

June 26, 2025,Giro in bici da corsa ad anello fino Montepulciano

Starting from San Quirico d'Orcia, we cycle through the rolling hills of the Val d'Orcia, along scenic roads offering spectacular views of cypress trees, cultivated fields, and medieval villages. We pass through Pienza, a splendid Renaissance town ideal for a brief stop. From here, the road gently climbs towards Montepulciano, particularly the 16th-century church of San Biagio.
On the way …

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July 19, 2025,Giro in bici da corsa ad anello da San Quirico a Chianciano

A stunning loop of approximately 60 km through the Tuscan hills, starting in San Quirico d'Orcia. It passes through Pienza, Monticchiello, and Montepulciano, gently climbing to Chianciano Terme, before returning via the southern Lucciola Bella Nature Reserve and Bagno Vignoni. The route is almost entirely paved, with gentle climbs, scenic descents, and breathtaking views of the Val d'Orcia and Val …

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Montepulciano – Historic Centre of Pienza loop from Montepulciano

Church of St. Agnes

Montepulciano

Church of San Biagio

Massaini Castle

View of Val d'Orcia

Historic center of San Quirico d'Orcia

Pienza, City of Pius II

Historic Centre of Pienza

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