5.0
(2)
60
riders
Monticchiello Gate – Historic Centre of Pienza loop from Monticchiello
05:28
99.2km
2,000m
Road cycling
Hard road ride. Very good fitness required. Some segments of this route may be unpaved and difficult to ride. The starting point of the route is accessible with public transport.
Last updated: May 9, 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 3.49 km for 491 m
After 58.1 km for 312 m
After 65.9 km for 121 m
Waypoints
Start point
Bus stop
Get Directions
11 m
Monticchiello Gate
Highlight • Historical Site
Translated by Google •
Tip by
4.54 km
Cypress Road to Pienza
Highlight • Trail
6.62 km
Pienza, City of Pius II
Highlight • Settlement
8.36 km
Historic Centre of Pienza
Highlight • Historical Site
He thus entrusted the total renovation of the village to the architect Bernardo Rossellino and the humanist Leon Battisti Alberti, who in just four years, from 1459 to 1462, defined the harmonious and typically fifteenth-century appearance of what would have been Pienza today.
Thus was born that is now known as the ideal city of author: "born from a thought of love and a dream of beauty", as Giovanni Pascoli wrote.
Due to its peculiar characteristics in 1996, together with the whole Val d’Orcia, Pienza was recognized as a World Heritage Site.
Walking through the historic center, in Piazza Pio II, a visit to the Duomo, the Cathedral of the Assumption, is a must. Inside it houses important and remarkable paintings by the most renowned artists of the time, while the beautiful octagonal bell tower rises above the ancient crypt.
In front of the Cathedral you can see the Palazzo Comunale, a historic building dating back to the mid-1400s with its main feature: the large loggia on the facade. Also in the main square, the imposing Museo-Palazzo Piccolomini stands out with its hanging garden from which you can admire a truly unique panorama over the entire Val d'Orcia, from Montalcino to Monte Amiata. To complete the closure of the central square, you can visit the Palazzo Borgia, seat of the Diocesan Museum of Pienza.
Inside the former San Carlo conservatory, there is now the Archaeological Museum of Pienza, a building of medieval origin, with archaeological and Etruscan collections on display and an exhibition itinerary that documents the urban and architectural history of the Pienza area.
A few steps from the historic center, a short walk takes you to the Pieve di Corsignano: a Romanesque church with three naves, whose origins date back to the 7th century.
Translated by Google •
Tip by
8.59 km
Pienza Historic Center and View of Val d'Orcia
Highlight • Historical Site
Translated by Google •
Tip by
42.3 km
Monte Amiata Climb
Highlight (Segment) • Climb
Translated by Google •
Tip by
54.4 km
Mount Amiata Summit (Vetta Amiata)
Highlight • Summit
Tip by
65.9 km
Former Mine of Abbadia San Salvatore
Highlight • Historical Site
99.2 km
End point
Bus stop
Way Types & Surfaces
Way Types
88.7 km
8.73 km
1.16 km
669 m
Surfaces
97.9 km
1.07 km
331 m
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Elevation
Highest point (1,660 m)
Lowest point (280 m)
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Weather
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Friday 29 May
29°C
11°C
0 %
Additional weather tips
Max wind speed: 8.0 km/h
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Our route recommendations are based on thousands of hikes, rides, and runs completed by other people on komoot.