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Italy
Tuscany
Siena
San Quirico D'Orcia

Val d'Orcia Loop: San Quirico, Pienza & Montepulciano

Routes
Road cycling routes
Italy
Tuscany
Siena
San Quirico D'Orcia

Val d'Orcia Loop: San Quirico, Pienza & Montepulciano

Hard

43

riders

Val d'Orcia Loop: San Quirico, Pienza & Montepulciano

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

A

Start point

Parking

Get Directions

1

194 m

Historic center of San Quirico d'Orcia

Highlight • Historical Site

San Quirico d'Orcia is one of the most historic and beautiful centers in the entire Val d'Orcia. Its history is thousands of years old and the center of San Quirico d'Orcia remains a real wedding favor. Furthermore, the Horti Leonini are an example of classic Italian gardens.

Translated by Google •

Tip by

2

9.44 km

Village Square, Castiglione d'Orcia

Highlight • Settlement

In the heart of the Val d'Orcia, a few kilometers from Bagno Vignoni, Pienza and Montalcino.
From the SS2 Cassia you climb regularly for 6 km at an average 5%, fully enjoying the views of the Val d'Orcia and the Borgo.

Translated by Google •

Tip by

3

45.5 km

Legendary Road of Monticchiello

Highlight (Segment) • Viewpoint

A wonderful road nestled in the Sienese hills, every glance you give at the panorama will be a memory that will remain with you forever.

Translated by Google •

Tip by

4

57.6 km

Montepulciano

Highlight • Settlement

Beautiful medieval village to visit. From the view of the vineyards to that of the Val d'Orcia, there is no shortage of views, not to mention the streets and alleys within the city walls. Unmissable Piazza Grande.

Translated by Google •

Tip by

5

67.8 km

Massaini Castle

Highlight • Castle

Among vineyards, olive groves and medicinal plants, stands Palazzo Massaini, a place where nature, tradition, Tuscan food and wine merge.
Source: palazzomassaini.com

Translated by Google •

Tip by

B

80.0 km

End point

Parking

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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

Elevation

Nothing selected – click and drag below to see the stats for a specific part of the route.

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.

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Frequently Asked Questions

What is the terrain like on this cycling route?

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.

Is this cycling route suitable for beginners?

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.

What are the main points of interest along the route?

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.

What kind of scenery can I expect while cycling?

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.

Where does the loop tour start, and is there parking available?

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.

How long does it typically take to complete this racebike tour?

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.

What is the best time of year to cycle this route?

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.

Are there any permits or entrance fees required for cycling in Val d'Orcia?

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.

Is this cycling route dog-friendly?

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.

Are there places to eat or stay along the route?

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.

Does the trail intersect other well-known paths?

Yes, the route briefly intersects with sections of the Ciclovia Francigena - VFB18 and EuroVelo 5 - Via Romea Francigena - part Italy, among other local paths.

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