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Road cycling routes

Historic Centre of Pienza – View of Val d'Orcia loop from Montepulciano

Road cycling routes

Historic Centre of Pienza – View of Val d'Orcia loop from Montepulciano

Hard

4.6

(9)

216

riders

Historic Centre of Pienza – View of Val d'Orcia loop from Montepulciano

04:31

86.3km

1,570m

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: April 16, 2026

Tips

Includes a segment in which cycling is not permitted

After 60.8 km for 259 m

Waypoints

A

Start point

Bus stop

Get Directions

1

8.70 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

2

12.6 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

3

20.2 km

View of Val d'Orcia

Highlight • Viewpoint

4

22.2 km

Capuchin Gate

Highlight • Historical Site

5

35.2 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 …

Translated by Google •

Tip by

6

35.5 km

View of Montalcino

Highlight (Segment) • Viewpoint

Where you can see a beautiful panorama.

Translated by Google •

Tip by

7

44.6 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.

Translated by Google •

Tip by

62.8 km

Viewpoint

Viewpoint

9

76.2 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

86.3 km

End point

Bus stop

Way Types & Surfaces

Way Types

45.4 km

39.3 km

1.55 km

< 100 m

Surfaces

86.1 km

290 m

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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 (670 m)

Lowest point (170 m)

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Weather

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Thursday 14 May

17°C

10°C

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Our route recommendations are based on thousands of hikes, rides, and runs completed by other people on komoot.

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