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Bike touring routes & trails
Italy
Tuscany
Siena

Crete Senesi Loop from Siena

Hard

4.6

(13)

202

riders

Crete Senesi Loop from Siena

04:45

71.6km

940m

Cycling

This difficult 44.5-mile touring bicycle loop from Siena to Asciano offers challenging climbs and stunning views of the Crete Senesi.

Last updated: February 26, 2026

Tips

Includes a segment in which cycling is not permitted

After 3.16 km for 197 m

Waypoints

A

Start point

Parking

Get Directions

1

3.59 km

Palazzo Pubblico and Piazza del Campo, Siena

Highlight • Historical Site

The Palazzo Pubblico is a palace in the center of Siena, near the old market, where today is the Municipal Museum. Every year, in front of Piazza del Campo, there is a local horse race, one of the cultural highlights of Siena.

Siena is considered one of the most beautiful cities in Italy and impresses with its mass of historical buildings, with which it has preserved its medieval character. The old town is a UNESCO World Heritage Site.

Translated by Google •

Tip by

2

4.64 km

Porta Romana (Siena)

Highlight • Monument

Porta Romana is one of the ancient gates in the walls of Siena, located on the path of the ancient Via Cassia which looks south towards Rome.
Porta Romana is one of the ancient gates in the walls of Siena, located on the route of the ancient Via Cassia that looks south towards Rome.

Translated by Google •

Tip by

3

9.00 km

Via Francigena

Highlight • Trail

Beginning of the stretch of Via Francigena, a dirt road but easily pedaled even in gravel

Translated by Google •

Tip by

4

20.1 km

Historic Centre of Monteroni d'Arbia

Highlight • Historical Site

Monteroni d'Arbia is located between the Val d'Orcia and Siena, both UNESCO heritage sites. This area offers enchanting landscapes and preserves traces of the past such as the Via Francigena and the Grancia di Cuna. Nearby, you can visit the Church of Santi Jacopo e Cristoforo and the parish church of Corsano.

Translated by Google •

Tip by

5

36.6 km

Historic center of Asciano

Highlight • Historical Site

Immersed in the splendid panorama of the Crete Senesi, Asciano has been inhabited since ancient times (Assianum). This treasure trove of art and history offers numerous monuments and two highly appreciated museums: the Palazzo Corboli Museum and the Cassioli Museum. Furthermore, between the towns of Leonina and Mucigliani stands the Site Transitoire, a stone work by Jean-Paul Philippe.

Translated by Google •

Tip by

6

48.9 km

View of the Crete Senesi

Highlight • Viewpoint

The Crete Senesi area develops between Asciano, Buonconvento, Monteroni d'Arbia, Rapolano Terme, Trequanda and Montalcino, one of the most spectacular in Tuscany and the Val d'Orcia. It is a lunar landscape made up of expanses of clay, hills and valleys dotted with small villages, isolated farmhouses, dirt roads flanked by long rows of cypresses.

Translated by Google •

Tip by

B

71.6 km

End point

Parking

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Way Types & Surfaces

Way Types

51.2 km

12.3 km

5.07 km

2.05 km

1.10 km

< 100 m

Surfaces

63.7 km

2.67 km

2.36 km

2.19 km

789 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 (340 m)

Lowest point (160 m)

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Weather

Powered by Foreca

Sunday 10 May

23°C

13°C

25 %

Additional weather tips

Max wind speed: 21.0 km/h

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This route was planned by komoot.

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Frequently Asked Questions

How challenging is the From Siena to Asciano – loop tour?

This loop tour is classified as difficult and requires very good fitness. You'll encounter significant elevation changes with numerous ascents and descents, some of which can be steep. The varied terrain, including unpaved sections and 'strade bianche,' adds to its demanding nature.

What kind of terrain will I encounter on this cycling route?

The route features varied terrain. While much of it is paved, you will ride on significant sections of unpaved roads, compacted gravel, and even some cobblestones. A distinctive feature is the presence of 'strade bianche,' the iconic white dirt roads of Tuscany. Be prepared for rolling hills and steep climbs.

What are the main points of interest along the From Siena to Asciano – loop tour?

You'll pass by several notable sights. In Siena, you can see the Palazzo Pubblico and Piazza del Campo and Porta Romana. The route also includes sections of the historic Via Francigena. Further along, you'll find the Historic Centre of Monteroni d'Arbia and the Historic center of Asciano. Don't miss the stunning View of the Crete Senesi.

Does this cycling route intersect with other well-known trails?

Yes, the route overlaps with several official trails. You'll find sections that are part of the EuroVelo 5 - Via Romea Francigena - part Italy, Ciclovia Francigena - VFB17, Via Lauretana Toscana, Via Francigena - 06 Tuscany, and the famous Strade Bianche and L'Eroica routes.

What is the best time of year to cycle this loop tour?

Spring (April-May) and early autumn (September-October) are generally the best times. The weather is milder, and the Tuscan landscape is particularly beautiful. Summers can be very hot, making the challenging climbs even more demanding, while winters can be cold and wet.

Are there any permits or entrance fees required for cycling in the Crete Senesi area?

No, there are no specific permits or entrance fees required to cycle this loop tour through the Crete Senesi. The area is largely open for public access. However, always respect private property and local regulations.

Is the From Siena to Asciano – loop tour suitable for families or beginners?

Given its 'difficult' classification, significant elevation changes, and varied terrain including unpaved sections, this loop tour is not recommended for beginners or families with young children. It requires very good fitness and cycling skills.

Where can I park my car to start this cycling tour in Siena?

For starting in Siena, you can look for parking options near the city center or the train station. Parking availability can vary, especially during peak season, so it's advisable to arrive early or research specific parking garages in advance.

Are dogs allowed on this cycling route?

While there are no specific restrictions against dogs on the public roads and paths that make up this route, it's important to consider the challenging nature of the ride and the varied terrain. If you bring a dog, ensure it is well-behaved, on a leash when appropriate, and capable of handling the distance and conditions, perhaps in a bike trailer.

What kind of scenery can I expect while cycling through the Crete Senesi?

You'll experience breathtaking scenery through the Crete Senesi, known for its unique 'lunar landscape.' Expect expansive clay hills, picturesque valleys, isolated farmhouses, and dirt roads beautifully lined with cypress trees. The route offers a rich blend of vineyards, olive groves, charming small towns, and the quintessential cultural landscapes of Southern Tuscany.

Are there places to stop for food or drinks along the route?

Yes, the route passes through several small towns like Monteroni d'Arbia and Asciano, where you can find cafes, restaurants, and shops to refuel. It's always a good idea to carry sufficient water and snacks, especially on longer stretches between towns.

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