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Road cycling routes
Italy
Tuscany
Siena
Montepulciano

View of Val d'Orcia – Montepulciano loop from Montepulciano

Routes
Road cycling routes
Italy
Tuscany
Siena
Montepulciano

View of Val d'Orcia – Montepulciano loop from Montepulciano

Moderate

4.0

(4)

63

riders

View of Val d'Orcia – Montepulciano loop from Montepulciano

02:24

49.7km

710m

Road cycling

Moderate road ride. 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 20, 2026

Tips

The surface for a segment of your route may not be suitable

Some segments of your route comprise a surface that may not be suitable for your chosen sport.

After 46.4 km for 85 m

Waypoints

A

Start point

Bus stop

Get Directions

1

3.07 km

Church of San Biagio

Highlight • Religious Site

Walking along the two parallel rows of cypresses it is possible to slowly glimpse the foreshortening of the bell tower that stands out high in the sky. And it seems …

Translated by Google •

Tip by

2

3.14 km

Temple of San Biagio

Highlight • Religious Site

Designed in the 16th century (start of construction 1518 - completion 1567) by Antonio da Sangallo the Elder. Typical example of Tuscan Renaissance architecture from the 16th century

Translated by Google •

Tip by

3

12.1 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 •

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4

24.0 km

Capuchin Gate

Highlight • Historical Site

5

26.0 km

View of Val d'Orcia

Highlight • Viewpoint

6

46.4 km

Montepulciano

Highlight • Settlement

Beautiful medieval village to visit. From the view of the vineyards to that of the Val d'Orcia, there is no shortage of views, not to mention the streets and alleys within the city walls. Unmissable Piazza Grande.

Translated by Google •

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7

47.6 km

Montepulciano

Highlight • Settlement

Montepulciano hidden and shrouded in fog

Translated by Google •

Tip by

8

48.2 km

Church of St. Agnes

Highlight • Religious Site

Baroque and neo-Romanesque style church.
It was built in 1306 by the abbess of Poliziana Agnese. At the end of the seventeenth century it was radically renovated.

Translated by Google •

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B

49.7 km

End point

Bus stop

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Way Types & Surfaces

Way Types

41.2 km

6.43 km

2.04 km

< 100 m

Surfaces

48.8 km

575 m

340 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 (580 m)

Lowest point (340 m)

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Weather

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Tuesday 14 July

36°C

19°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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