Montalcino – Montalcino Fortress loop from Castiglione d'Orcia

Montalcino – Montalcino Fortress loop from Castiglione d'Orcia

Hard

4.5

(6)

103

riders

Montalcino – Montalcino Fortress loop from Castiglione d'Orcia

03:46

61.8km

1,290m

Road cycling

Hard road ride. Very good fitness required. Some segments of this route may be unpaved and difficult to ride. The starting point of the route is right next to a parking lot.

Last updated: August 20, 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 9.87 km for 7.51 km

After 41.1 km for 131 m

Waypoints

Start point

Parking

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580 m

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%, …

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9.12 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 …

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9.43 km

San Quirico d'Orcia Historic Centre

Highlight • Historical Site

This is a wonderful village along the Via Francigena. It has an ancient history and is worth stopping for a visit. A UNESCO heritage site, San Quirico d'Orcia is a …

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20.4 km

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 …

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20.8 km

View of Montalcino

Highlight (Segment) • Viewpoint

Where you can see a beautiful panorama.

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29.8 km

Castelnuovo dell’Abate Village & View of Abbazia di Sant’Antimo

Highlight • Settlement

Castelnuovo dell'Abate is a fraction of the Italian municipality of Montalcino, in the province of Siena, in Tuscany.

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30.7 km

It is a former Benedictine monastic complex, located near Castelnuovo dell'Abate, within the municipality of Montalcino, in the province of Siena.
It is one of the most important architectures of the Tuscan Romanesque, dating back to the 4th century.

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40.5 km

Montalcino Fortress

Highlight • Castle

The historic center of Montalcino is dominated by the mighty Rocca, a fortress built in 1361 to mark the passage of the city under the dominion of Siena. The panorama …

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