San Quirico d'Orcia – Montalcino loop from Contignano

San Quirico d'Orcia – Montalcino loop from Contignano

Hard

riders

San Quirico d'Orcia – Montalcino loop from Contignano

03:15

67.8km

910m

Road cycling

Hard road ride. Very good fitness required. Mostly well-paved surfaces and easy to ride. The starting point of the route is right next to a parking lot.

Last updated: September 25, 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 20.3 km for 206 m

After 34.8 km for 131 m

Waypoints

Start point

Parking

Get Directions

354 m

Panoramic bench overlooking the Val d'Orcia

Highlight • Viewpoint

Recommended to go there around sunset time, really very nice.

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19.9 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 d'Orcia remains a real wedding favor. Furthermore, the Horti Leonini are an example of classic Italian gardens.

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20.3 km

Capuchin Gate

Highlight • Historical Site

20.6 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 living portrait of Tuscany, a place where every corner tells a story.

Translated by Google •

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20.8 km

San Quirico d'Orcia

Highlight • Settlement

One of the most beautiful villages in the Val d'Orcia

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33.7 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 is indeed renowned for its Sangiovese vineyards, from which we obtain the famous Brunello di Montalcino and which also produce two other AOC wines, Rosso di Montalcino and Sant'Antimo.

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34.2 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 that can be enjoyed from the ramparts of the fortress is truly spectacular; it goes from Monte Amiata, through the Crete up to Siena, and crosses the whole Val d'Orcia up to the Maremma hills.
Source, discovertuscany.com

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55.2 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

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67.8 km

End point

Parking

Way Types & Surfaces

Way Types

46.6 km

18.8 km

2.38 km

131 m

Surfaces