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Montalcino – View of Val d'Orcia loop from Montepulciano

Montalcino – View of Val d'Orcia loop from Montepulciano

Hard

4.3

(4)

riders

Montalcino – View of Val d'Orcia loop from Montepulciano

04:34

89.8km

1,510m

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: May 18, 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 42.6 km for 258 m

After 43.6 km for 131 m

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17.7 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

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42.6 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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43.0 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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58.2 km

Tuscan Vineyard Landscape

Highlight • Natural

I crossed it in the middle of August, the thermometer at 44 degrees, I will remember it for a long time...

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59.8 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 …

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