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Historic Centre of Pienza – Montepulciano loop from San Giovanni d'Asso

Historic Centre of Pienza – Montepulciano loop from San Giovanni d'Asso

Hard

4.8

(4)

100

riders

Historic Centre of Pienza – Montepulciano loop from San Giovanni d'Asso

03:54

72.9km

1,430m

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: June 23, 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 43.2 km for 267 m

After 43.9 km for 70 m

Waypoints

Start point

Train Station

Get Directions

2.93 km

Scavi Archeologici di Pava

Archaeological Site

9.31 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 …

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18.9 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 •

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20.8 km

Monticchiello Gate

Highlight • Historical Site

Rest of the city walls from the 13th century.

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30.0 km

Legendary Road of Monticchiello

Highlight (Segment) • Viewpoint

A wonderful road nestled in the Sienese hills, every glance you give at the panorama will be a memory that will remain with you forever.

Translated by Google •

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42.3 km

Montepulciano

Highlight • Settlement

Montepulciano hidden and shrouded in fog

Translated by Google •

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42.9 km

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 •

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43.3 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.

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72.9 km

End point

Train Station

Way Types & Surfaces

Way Types

61.0 km

8.98 km

2.88 km

< 100 m

Surfaces

71.7 km

1.15 km

< 100 m

Elevation

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

Highest point (670 m)

Lowest point (270 m)

Weather

Saturday 18 July

37°C

21°C

-- %

Additional weather tips

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Comments

October 13, 2025,Giro per Paesini

Tour to visit Castelmuzio, Petroio, Montefollonico and Pienza

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Historic Centre of Pienza – Montepulciano loop from San Giovanni d'Asso

Castelmuzio Historic Village

Historic Centre of Pienza

Pienza, City of Pius II

Monticchiello Gate

Legendary Road of Monticchiello

Montepulciano

Church of St. Agnes

Montepulciano

Nearby routes

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