5.0
(3)
9
riders
04:17
58.2km
960m
Cycling
This difficult 36.1-mile touring bicycle ring tour from Pienza to Lake Montepulciano offers challenging terrain and stunning Val d'Orcia vie
Last updated: February 26, 2026
Waypoints
Start point
Parking
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224ย m
Highlight โข Settlement
7.26ย km
Highlight (Segment) โข Viewpoint
Translated by Google โข
Tip by
14.7ย km
Highlight โข Settlement
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28.6ย km
Highlight โข Lake
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58.2ย km
End point
Parking
Way Types & Surfaces
Way Types
40.6ย km
7.13ย km
4.83ย km
4.21ย km
1.42ย km
Surfaces
40.9ย km
7.83ย km
5.67ย km
3.68ย km
191ย m
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Elevation
Highest point (580ย m)
Lowest point (250ย m)
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Weather
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Wednesday 13 May
20ยฐC
7ยฐC
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This route was planned by komoot.
This ring tour is classified as a difficult bike ride, requiring very good fitness. It features significant elevation gain and includes some unpaved, challenging segments where you might need to push your bike.
The route features a varied terrain, including a mix of paved roads, dirt roads, and gravel sections, famously known as 'strade bianche'. You will encounter rolling hills and valleys, contributing to substantial elevation changes.
The tour connects several culturally rich locations and offers stunning views. You'll pass through the Renaissance village of Pienza, the historic hilltop town of Historic Center of Montepulciano, and the Lago di Montepulciano Nature Reserve. You'll also enjoy panoramic views, including a View of Montepulciano and the Val d'Orcia.
The Val d'Orcia region is beautiful year-round, but spring (April-May) and autumn (September-October) generally offer the most pleasant cycling conditions with milder temperatures and vibrant landscapes. Summer can be very hot, making the challenging climbs more demanding.
No specific permits are required to cycle this route. While the tour passes through the Lago di Montepulciano Nature Reserve, there are typically no entrance fees for general access to the cycling paths within the reserve.
You can typically find parking in or around the towns of Pienza or Montepulciano, which serve as excellent starting points for this ring tour. Look for designated public parking areas in these towns.
While dogs are generally allowed on trails in the Val d'Orcia, this particular route is a challenging cycling tour. If you plan to bring a dog, ensure it is accustomed to long distances and varied terrain, and always keep it on a leash, especially near roads and in nature reserve areas.
Yes, this route shares sections with several other paths, including the Cammino d'Assisi, Barlettaia, EuroVelo 7 - Sun Route - part Italy 2, and the Sentiero della Via Barlettaia, among others.
You'll experience the iconic landscapes of the Val d'Orcia, a UNESCO World Heritage site. Expect breathtaking panoramic views of rolling hills, cypress-lined roads, vineyards producing Vino Nobile di Montepulciano, and charming Tuscan farmhouses. Some areas were even filming locations for movies like 'Gladiator'.
Absolutely. The region is renowned for its gastronomic culture. Both Pienza and Montepulciano offer excellent opportunities for food and wine tastings, including local pecorino cheese in Pienza and Vino Nobile di Montepulciano in Montepulciano, with options to visit underground cellars.
Given the difficulty and varied terrain, it's essential to pack appropriate cycling gear, including a helmet, repair kit, sufficient water, snacks, and weather-appropriate clothing. Consider a mountain bike or a sturdy touring bike suitable for gravel sections. Don't forget your camera for the stunning views!