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Italy
Tuscany
Siena
Montalcino

From Montalcino to Castiglione d'Orcia – loop tour

Routes
Road cycling routes
Italy
Tuscany
Siena
Montalcino

From Montalcino to Castiglione d'Orcia – loop tour

Hard

4.2

(9)

272

riders

From Montalcino to Castiglione d'Orcia – loop tour

02:46

50.2km

1,090m

Road cycling

Embark on a difficult road cycling loop from Montalcino to Castiglione d'Orcia, covering 31.2 miles (50.2 km) with a significant 3573 feet (1089 metres) of elevation gain. This challenging route, which you can complete in about 2 hours and 45 minutes, winds through Tuscany's Val d'Orcia region. You will experience…

Last updated: April 23, 2026

Waypoints

A

Start point

Parking

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1

142 m

Montalcino

Highlight • Settlement

Positioned on top of a hill, overlooking the Ombrone and Asso valleys, Montalcino is fortunate to be at the center of one of Tuscany's most important wine regions. The territory …

Translated by Google •

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2

13.6 km

Orcia River Crossing

Highlight • Bridge

The bridge near the Monte Amiata station offers a very beautiful view of the Val d'Orcia.

Translated by Google •

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3

24.6 km

Village Square, Castiglione d'Orcia

Highlight • Settlement

In the heart of the Val d'Orcia, a few kilometers from Bagno Vignoni, Pienza and Montalcino.
From the SS2 Cassia you climb regularly for 6 km at an average 5%, …

Translated by Google •

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4

33.8 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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B

50.2 km

End point

Parking

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Way Types & Surfaces

Way Types

32.5 km

16.3 km

1.36 km

Surfaces

50.2 km

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Elevation

Elevation

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

Highest point (590 m)

Lowest point (170 m)

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Weather

Powered by Foreca

Friday 29 May

29°C

12°C

0 %

Additional weather tips

Max wind speed: 14.0 km/h

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This route was planned by komoot.

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318

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