Val d'Orcia Loop: San Quirico, Pienza & Montepulciano
Val d'Orcia Loop: San Quirico, Pienza & Montepulciano
43
riders
04:07
80.0km
1,420m
Road cycling
This difficult 49.7-mile road cycling loop from San Quirico d'Orcia to Montepulciano offers challenging climbs and iconic Val d'Orcia views.
Last updated: February 26, 2026
Waypoints
Start point
Parking
Get Directions
194 m
Highlight • Historical Site
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Tip by
9.44 km
Highlight • Settlement
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Tip by
45.5 km
Highlight (Segment) • Viewpoint
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Tip by
57.6 km
Highlight • Settlement
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Tip by
67.8 km
Highlight • Castle
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Tip by
80.0 km
End point
Parking
Way Types & Surfaces
Way Types
44.0 km
34.1 km
1.80 km
< 100 m
Surfaces
79.1 km
497 m
448 m
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Elevation
Highest point (790 m)
Lowest point (260 m)
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Weather
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Wednesday 13 May
21°C
9°C
0 %
Additional weather tips
Max wind speed: 26.0 km/h
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This route was planned by komoot.
This route primarily features hilly landscapes with significant elevation changes, characteristic of the Val d'Orcia. While most surfaces are well-paved, be prepared for some segments that may be unpaved or difficult, potentially requiring you to dismount and push your bike. It demands very good fitness.
No, this route is generally considered difficult and is best suited for experienced road cyclists with very good fitness due to its challenging elevation changes and distance.
The loop tour offers numerous highlights. You'll pass through the historic center of San Quirico d'Orcia, the charming Village Square, Castiglione d'Orcia, and the iconic Legendary Road of Monticchiello. The route also takes you to Montepulciano and past Massaini Castle, all set within the stunning Val d'Orcia.
Expect breathtaking panoramic views of the UNESCO World Heritage-listed Val d'Orcia. You'll cycle through peaceful country roads lined with cypress trees, lush green fields, vineyards, and golden wheat fields, dotted with beautifully preserved medieval and Renaissance villages.
The loop tour typically starts in San Quirico d'Orcia. Parking is generally available in and around the town, though it's advisable to check local regulations or the visitsanquirico.it website for specific parking information.
This racebike tour is approximately 80 km long with over 1,400 meters of elevation gain. On average, it takes about 4 hours and 8 minutes of active cycling time, but this can vary significantly based on your fitness level and how often you stop to enjoy the scenery.
The best times to cycle in Val d'Orcia are spring (April-May) and autumn (September-October). During these seasons, the weather is generally pleasant, and the landscapes are particularly vibrant with blooming flowers or rich autumn colors. Summers can be very hot, and winters can be cold and wet.
No, there are no specific permits or entrance fees required for cycling on public roads and trails within the Val d'Orcia region, which is a UNESCO World Heritage site. However, always respect private property and local regulations.
While the route itself is on public roads, bringing a dog on a racebike tour of this difficulty and length is generally not recommended. If you plan to stop in towns, always check local pet policies for shops, restaurants, and accommodations.
Yes, both San Quirico d'Orcia and Montepulciano, as well as smaller villages like Castiglione d'Orcia, offer various options for cafes, restaurants, and accommodation. Montepulciano is particularly known for its wine and culinary scene, making it a great stop for refreshments.
Yes, the route briefly intersects with sections of the Ciclovia Francigena - VFB18 and EuroVelo 5 - Via Romea Francigena - part Italy, among other local paths.