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Monticchiello – Montepulciano loop from Pienza

Monticchiello – Montepulciano loop from Pienza

Hard

5.0

(2)

riders

Monticchiello – Montepulciano loop from Pienza

02:51

32.7km

890m

Gravel riding

Hard gravel ride. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels. The starting point of the route is right next to a parking lot.

Last updated: June 25, 2026

Waypoints

Start point

Parking

Get Directions

85 m

Pienza Historic Center and View of Val d'Orcia

Highlight • Historical Site

Immersed in the green heart of the Val d'Orcia, Pienza stands before your eyes like a Renaissance monument solidified over time. Pope Pius II wanted it and built it as an ideal city, and since then its beauty has been preserved intact. As you stroll through its silent streets, savor the serenity and beauty of a village where art and history blend with the breathtaking Tuscan landscape.

Translated by Google •

Tip by

5.11 km

Panoramic view

Highlight • Viewpoint

This view motivates you to continue driving to the next ice cream parlor!

Translated by Google •

Tip by

7.03 km

View of the countryside between Pienza and Monticchiello

Highlight • Viewpoint

It's always worth it, but spring is the most beautiful time

Translated by Google •

Tip by

7.76 km

Monticchiello

Highlight • Settlement

Beautiful Tuscan Hill town.

Tip by

7.87 km

View of Montepulciano and the Val d'Orcia

Highlight (Segment) • Viewpoint

Steep gravel. Just not made for the racing bike!

Translated by Google •

Tip by

14.4 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 that it competes with the tips of the cypresses, which manage to keep up with the tower as long as the perspective works in their favor.
And it is right here, in the area where the Val d'Orcia intertwines with the Valdichiana, that we can find the beautiful temple of San Biagio.

Translated by Google •

Tip by

15.5 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 •

Tip by

16.6 km

Town Hall of Montepulciano

Highlight • Historical Site

Overlooking Piazza Grande, the Palazzo Comunale is one of Montepulciano's symbolic buildings. Originally from the 13th century and reworked by Michelozzo in the 15th century, it echoes the forms of Florence's Palazzo della Signoria, desired by Cosimo I. From the visitable tower, a breathtaking panorama opens up.

Showing Translation

Tip by

32.7 km

End point

Parking

Way Types & Surfaces

Way Types

15.0 km

11.7 km

4.71 km

1.29 km

Surfaces

15.0 km

11.1 km

3.99 km

1.54 km

1.13 km

Elevation

Nothing selected – click and drag below to see the stats for a specific part of the route.

Highest point (600 m)

Lowest point (320 m)

Weather

Wednesday 8 July

34°C

17°C

17 %

Additional weather tips

Max wind speed: 9.0 km/h

to get more detailed weather forecasts along your route

Comments

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Monticchiello – Montepulciano loop from Pienza

Pienza Historic Center and View of Val d'Orcia

Panoramic view

View of the countryside between Pienza and Monticchiello

Monticchiello

View of Montepulciano and the Val d'Orcia

Church of San Biagio

Montepulciano

Town Hall of Montepulciano

Nearby routes

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