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Road cycling routes

Castiglione D'Orcia

Historic Centre of Pienza – View of Monte Amiata loop from Bagni San Filippo

Road cycling routes

Castiglione D'Orcia

Historic Centre of Pienza – View of Monte Amiata loop from Bagni San Filippo

Hard

5.0

(3)

39

riders

Historic Centre of Pienza – View of Monte Amiata loop from Bagni San Filippo

03:50

78.8km

1,140m

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: October 9, 2026

Waypoints

A

Start point

Bus stop

1

13.1 km

View of the Cypress-Lined Villa in Tuscany

Highlight • Viewpoint

Absolute photo highlight spot - unfortunately also known to many other tourists ;-)

Translated by Google •

Tip by

2

18.3 km

Spedaletto Castle

Highlight • Castle

This is the Spedaletto castle: "a fortified architectural complex located in the rural locality of the same name in the municipal area of Pienza along the Provincial Road 53".
Source: artsandculture.google.com/entity/castle-of-spedaletto/g11b5m68f7b?hl=en

Translated by Google •

Tip by

3

26.2 km

Pienza, City of Pius II

Highlight • Settlement

4

27.9 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 •

Tip by

5

31.8 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

6

40.7 km

Avenue of Remembrance

Highlight • Monument

Conceived as a monumental link between the Temple of S. Biagio and the Old Cemetery, it consists of two rows of cypresses arranged on the sides of the road. At …

Translated by Google •

Tip by

7

47.4 km

View of Monte Amiata

Highlight • Viewpoint

The best view of Monte Amiata over the southern part of Valdorcia

Tip by

8

49.8 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 •

Tip by

B

78.8 km

End point

Bus stop

Way Types & Surfaces

Way Types

55.1 km

23.0 km

596 m

107 m

< 100 m

< 100 m

Surfaces

78.2 km

345 m

245 m

< 100 m

< 100 m

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Elevation

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

Highest point (670 m)

Lowest point (250 m)

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Weather

Powered by Foreca

Sunday 11 October

21°C

11°C

36 %

Additional weather tips

Max wind speed: 17.0 km/h

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