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Historic Centre of Pienza – Asciano Historic Center loop from Monteroni d'Arbia

Historic Centre of Pienza – Asciano Historic Center loop from Monteroni d'Arbia

Hard

riders

Historic Centre of Pienza – Asciano Historic Center loop from Monteroni d'Arbia

05:36

115km

1,670m

Road cycling

Hard road ride. Very good fitness required. Mostly well-paved surfaces and easy to ride. The starting point of the route is accessible with public transport.

Last updated: July 11, 2026

Tips

The surface for a segment of your route may not be suitable

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

After 36.1 km for 240 m

Waypoints

Start point

Train Station

Get Directions

12.9 km

Historic Center of Buonconvento

Highlight • Historical Site

The small village of Buonconvento is located within the municipality of Siena and rises along the ancient Via Francigena. It has a small but fascinating historic centre, where the main church, the town hall and two museums are located.

Let yourself be fascinated by the typical red brick architecture and the different picturesque corners to take some great photos!

Translated by Google •

Tip by

23.5 km

Locanda Paradiso, Chiusure

Highlight • Restaurant

In Chiusure there is a nice little place. Here you can relax and take a nice break. The view of the valley is very nice. In the small restaurant "Locanda Paradiso" you can take a little something. Opening hours: 12:30 - 14:30, 19:30 - 21:30 (no guarantee)

Translated by Google •

Tip by

25.3 km

View of the Chiusure Valley

Highlight (Segment) • Viewpoint

32.3 km

Scavi Archeologici di Pava

Archaeological Site

36.2 km

Palazzo Mannucci Benincasa

Castle

39.3 km

Castelmuzio Historic Village

Highlight • Settlement

Very nice old village at the top of the hill, with its narrow roads, stone houses, and typical views on the hills around. There's a very quiet terrace with some tables and chairs where you can sit and enjoy the great panorama.

Tip by

48.3 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 he became Pope, wanted to transform his humble hometown, Corsignano, in an urban-architectural treasure.
He thus entrusted the total renovation of the village to the architect Bernardo Rossellino and the humanist Leon Battisti Alberti, who in just four years, from 1459 to 1462, defined the harmonious and typically fifteenth-century appearance of what would have been Pienza today.
Thus was born that is now known as the ideal city of author: "born from a thought of love and a dream of beauty", as Giovanni Pascoli wrote.
Due to its peculiar characteristics in 1996, together with the whole Val d’Orcia, Pienza was recognized as a World Heritage Site.

Walking through the historic center, in Piazza Pio II, a visit to the Duomo, the Cathedral of the Assumption, is a must. Inside it houses important and remarkable paintings by the most renowned artists of the time, while the beautiful octagonal bell tower rises above the ancient crypt.

In front of the Cathedral you can see the Palazzo Comunale, a historic building dating back to the mid-1400s with its main feature: the large loggia on the facade. Also in the main square, the imposing Museo-Palazzo Piccolomini stands out with its hanging garden from which you can admire a truly unique panorama over the entire Val d'Orcia, from Montalcino to Monte Amiata. To complete the closure of the central square, you can visit the Palazzo Borgia, seat of the Diocesan Museum of Pienza.

Inside the former San Carlo conservatory, there is now the Archaeological Museum of Pienza, a building of medieval origin, with archaeological and Etruscan collections on display and an exhibition itinerary that documents the urban and architectural history of the Pienza area.

A few steps from the historic center, a short walk takes you to the Pieve di Corsignano: a Romanesque church with three naves, whose origins date back to the 7th century.

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Tip by

52.2 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

67.8 km

Castello dei Cacciaconti

Castle

99.2 km

Asciano Historic Center

Highlight • Settlement

During the annual Eroica event, a kind of vintage racing bike tour with thousands of participants, there is a refreshment station in Asciano. The locals then serve fine Italian snacks and of course red wine from the region. It is not that comfortable without the event, but the city will inspire you and you will also get your money's worth when it comes to food.

Translated by Google •

Tip by

114 km

San Fabiano Countryside View

Highlight • Viewpoint

Perfect starting point for numerous tours.

Translated by Google •

Tip by

115 km

End point

Train Station

Way Types & Surfaces

Way Types

95.1 km

16.4 km

3.11 km

175 m

< 100 m

Surfaces

114 km

703 m

371 m

Elevation

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

Highest point (560 m)

Lowest point (140 m)

Weather

Tuesday 14 July

38°C

19°C

0 %

Additional weather tips

Max wind speed: 15.0 km/h

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Historic Centre of Pienza – Asciano Historic Center loop from Monteroni d'Arbia

Historic Center of Buonconvento

Locanda Paradiso, Chiusure

View of the Chiusure Valley

Castelmuzio Historic Village

Historic Centre of Pienza

Massaini Castle

Asciano Historic Center

San Fabiano Countryside View

Nearby routes

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