The best road cycling routes around Pienza
4.5
(38)
1,069
riders
27
rides
Last updated: October 25, 2025
4.1
(13)
235
riders
1. Historic Center of Pienza – Historic Center of Pienza loop from Monticchiello
60.2km
03:20
1,140m
1,140m
Expert road ride. Very good fitness required. Some segments of this route may be unpaved and difficult to ride.
41
riders
2. Porta di Monticchiello – Tuscan Vineyard Landscape loop from Monticchiello
70.9km
03:35
1,080m
1,080m
Expert road ride. Very good fitness required. Some segments of this route may be unpaved and difficult to ride.
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36
riders
3. View of Val d'Orcia loop from Pian del Nocio
18.8km
00:55
250m
250m
Easy road ride. Great for any fitness level. Mostly well-paved surfaces and easy to ride.
29
riders
4. Avenue of Remembrance – Montepulciano loop from Gallina
30.1km
01:47
720m
720m
Intermediate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.
4.5
(2)
57
riders
5. Historic Center of Pienza – Historic Center of Pienza loop from Pienza
29.5km
01:25
410m
410m
Intermediate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.
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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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