4.5
(1856)
17,978
riders
72
rides
No traffic touring cycling routes around Pienza traverse the undulating hills of Val d'Orcia, a UNESCO World Heritage Site in Tuscany. The region is characterized by cultivated fields, vineyards, olive groves, and distinctive cypress-lined avenues. Cyclists encounter both well-maintained country lanes and unpaved "white roads," offering varied terrain. The landscape also features the unique "Crete Senesi," barren clay hills that provide a striking contrast to the verdant valleys.
Last updated: June 3, 2026
4.0
(4)
61
riders
13.4km
01:13
380m
380m
Moderate bike ride. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.
3.4
(9)
71
riders
Moderate bike ride. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.

Sign up for free
4.5
(2)
18
riders
16.2km
01:29
500m
500m
Hard bike ride. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.
5.0
(1)
25
riders
24.5km
02:17
600m
600m
Hard bike ride. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.
3.4
(10)
82
riders
Moderate bike ride. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.
Get access to more routes and recommendations from other explorers.
Sign up for free
Already have an account?
Our route recommendations are based on thousands of hikes, rides, and runs completed by other people on komoot.
Start today with a free account
Your next adventure awaits.
Login or Signup
Popular around Pienza
pretty here, very pretty
0
0
The Collegiate Church of Saints Quirico and Giulitta is the main church of San Quirico d’Orcia and is located in the historic center of the village. The building has Romanesque origins and over time has undergone modifications that have added Gothic and Renaissance elements. The facade features three sculpted portals and a central rose window, while the interior preserves works and decorations from different eras. The collegiate church is dedicated to Saints Quirico and Giulitta, Christian martyrs, and represents one of the historical and religious landmarks of the town.
1
0
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.
0
0
Chiesa di Santa Maria Assunta The church, dating to the twelfth century, has a plain rectangular plan with a wall covering in square stones. Outside the massive portal is embellished with decorations, maybe originating from the Abbazia di Sant'Antimo. The gabled bell tower and the vestry are original, too. The apse is crowned with corbels and decorated with suspended arches. On the left side there is another monumental portal whose arch is supported by two columns and contains a decorated shape. The extremely plain interior is lit up by narrow slits, one in the apse.
0
0
Beautiful little place with a tower
0
0
There are over 60 dedicated no-traffic touring cycling routes around Pienza, offering a wide range of experiences for cyclists. These include 1 easy route, 32 moderate routes, and 34 difficult routes, ensuring options for various skill levels.
Yes, Pienza offers a variety of no-traffic touring cycling routes for all skill levels. While many routes are moderate to difficult, there is at least one easy route available, making it possible for beginners and families to enjoy the stunning Val d'Orcia landscapes without heavy traffic.
The Val d'Orcia region, including Pienza, is beautiful year-round. For pleasant cycling conditions and to potentially avoid peak tourist traffic, spring (April-May) and autumn (September-October) are often recommended. The weather is generally mild, and the landscapes are particularly vibrant.
You can expect to cycle through the iconic rolling hills of the Val d'Orcia, a UNESCO World Heritage Site, characterized by cultivated fields, vineyards, olive groves, and winding cypress-lined avenues. Some routes may also take you through the unique 'Crete Senesi,' a lunar-like terrain of barren clay hills, offering a striking contrast.
Yes, many of the no-traffic touring cycling routes around Pienza are designed as loops. For example, the View of Pienza – Pienza loop from Pienza offers a moderate 12.7 km ride with scenic views, starting and ending in Pienza.
Many routes pass through or near charming towns and significant landmarks. You can explore the historic center of Pienza itself (Pienza), or visit nearby medieval hamlets like Monticchiello. Other routes might lead you to San Quirico d'Orcia Historic Centre or the Historic town of Montalcino, each offering unique cultural insights.
Yes, the region is dotted with historic fortifications. Depending on your chosen route, you might pass by or have views of structures like Spedaletto Castle, the Montalcino Fortress, or the impressive Radicofani Fortress. These offer great opportunities for a historical stop.
Absolutely. The Historic Center of Montepulciano – Avenue of Remembrance loop from Pienza is a challenging 24.4 km route that provides stunning views and takes you towards Montepulciano, known for its wine and historic center.
The no-traffic touring cycling routes around Pienza are highly rated by the komoot community, with an average score of 4.56 stars. Reviewers often praise the breathtaking panoramic views of the Val d'Orcia, the tranquility of the 'white roads,' and the opportunity to discover charming Tuscan villages and historic sites along the way.
Yes, the iconic cypress tree formations are a frequent sight in the Val d'Orcia. While not explicitly listed in the routes provided, many paths in the region, such as those near Monticchiello, will offer glimpses of these beloved landmarks, including the famous 'Gladiator's Cypresses'.
Yes, there are routes that connect these two beautiful towns. The Monticchiello – Viale delle Rimembranze loop from Monticchiello is a challenging 16.1 km route that allows you to explore the area between Monticchiello and Pienza, offering picturesque views of the Val d'Orcia.


Browse the best Cycling routes in other regions.