Guided cycling holiday in Tuscany on the world's most famous white roads. Start your self-supported gravel tour in the splendid Val d'Orcia among vineyards, natural reserves and wonderful landscapes.

Val d'Orcia Gravel

789,00 € p.p.
Guided Tour
Duration 6 days

Departure Date

Adventure Bike
Single room supplement


This tour will be activated from a minimum of 6 participants up to a maximum of 12 participants

The rolling hills and rows of cypresses, the boundless environments and the vineyards of Chianti and Brunello. Tuscany is the rediscovery of the ancient flavors of a rural culture, a symbol of excellence all over the world. The Strade Bianche and the permanent route of the Eroica are unique and pedaling within the Val d’Orcia and Val di Merse along a fantastic gravel tour will only give you a smile for an unforgettable cycling holiday. You will be amazed as you go up and down the lunar environments of the Crete Senesi, a clay carpet shaped by the elements millions of years ago and now the cradle of the precious white truffle, the diamond of the Crete. There will be no shortage of climbs or descents, but at every bend you will stop to immortalize ever-changing landscapes and keep them in your heart forever. The realm of the dirt road, of crazy villages clinging to the hills, of gravel to the nth degree: a dream for lovers of cycling and good food. You will definitely not go dry!

Stage by stage


Val d'Orcia Guided Gravel Bike Tour is a 340 km (211 miles) guided bike tour that develops between the provinces of Siena and Grosseto along the characteristic white roads of Tuscany. It is a ring tour with significant differences in height and allows you to cross historic villages, areas with a strong landscape interest and valuable areas of wine production.

1st stage: Buonconvento – Pienza

(63 km 1200m D+: paved 15%; gravel 85%)(39 miles 3937 feet elevation gain)

Under the bells of the church of Saints Peter and Paul, the adventure begins, which from Buonconvento in the province of Siena leads to the heights of the Crete Senesi, near the magnificent abbey of Monte Oliveto Maggiore. Continuing with alternating climbs and descents on gravel paths, we reach the base of the hill on which the famous town of Montalcino stands. Between fantastic hilly environments embellished with rows of cypresses, you cross San Quirico d’Orcia before ending the day in Pienza.

2nd stage: Pienza – Ponte a Rigo

(66 km 1500m D+: paved 30%; gravel 70%)(41 miles 4921 feet elevation gain)

From the World Heritage Site where some scenes of the film The Gladiator were shot, we head first to the ancient Roman baths of Bagno Vignoni and then to the imposing Rocca Tentennano adjacent to Castiglione d’Orcia. Through the Via Francigena you reach the Rocca di Radicofani, which in effect represents the icing on the cake of this magnificent day on the pedals that will end a little further on, in Ponte a Rigo.

3rd stage: Ponte a Rigo – Montalcino

(65 km 1950m D+: paved 50%; gravel 50%)(40 miles 6397 feet elevation gain)

From Ponte a Rigo you enter the lands that form the background of the most representative mountain of this magnificent area: Mount Amiata, which with its 1738 m of altitude dominates the Val d'Orcia and Val di Paglia delimiting the provinces of Siena and Grosseto. Continuing along its eastern side, you cross Abbadia San Salvatore and the village of Vivo d’Orcia before entering the province of Grosseto and resting your bicycle on the walls of Seggiano. Between pleasant ups and downs and imposing historical monuments you reach the gates of Montalcino, a Sienese town where the precious Brunello wine is produced.

4th stage: Montalcino – Casciano

(43 km 700m D+: paved 25%; gravel 75%)(26,7 miles 2296 feet elevation gain)

In this fourth stage the attractions will not be lacking, starting from the dirt roads and the permanent route of the Eroica that have made this region famous. You pass the Brunello di Montalcino production area and end the day pedaling on the daring route of the old railway of the Murlo mine, an experience that smells of a past linked to the extraction of lignite.

5th stage: Casciano – Rosia

(62 km 1100m D+: paved 50%; gravel 50%)(38,5 miles 3608 feet elevation gain)

From the town of Casciano you enter the Basso Merse Nature Reserve located in the namesake valley. From the contiguous thermal area of Bagni di Petriolo, reachable through a fun gravel route, continue in the woods of the wild Val di Merse between climbs and descents on dirt roads until you reach the suggestive abbey of San Galgano and the village of Rosia, with views of the nearby metalliferous hills.

6th stage: Rosia – Buonconvento

(41 km 500m D+: paved 40%; gravel 60%)(25,4 miles 1640 feet elevation gain)

On the last day of pedaling, you leave the Alto Merse Nature Reserve behind you and touch the medieval core of Stigliano and continue in hilly environments embellished by villages and fairytale settings. Once at the gates of Siena, turn south along pleasant dirt roads with excellent pedalability until the end of the gravel loop tour in Buonconvento.

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Tuscany Gravel

Cypress trees and white roads

Ride on the most iconic white roads in Val d'Orcia and Val di Merse, known for L'Eroica and Strade Bianche

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  • Buonconvento and the Crete Senesi
  • The historic centre UNESCO site of Pienza
  • The Strade Bianche and the permanent route of l'Eroica by bicycle
  • Finocchiona and Brunello wine D.O.C.G., Cantucci and Vinsanto
  • The historic abbeys of Sant' Antimo and San Galgano
  • The old railway of Murlo
  • Followinf Sigeric's path along Via Francigena
  • The val di Merse Natural Reserve
  • Bagno Vignoni and the ancient Roman baths
  • The endless cypress trees rows in val d'Orcia


Overnight stays are provided in a 3* or 4* hotels in a double room with private facilities. If the facilities are not available, we will guarantee alternative accommodation of the same level in locations not far away.

Type of terrain

This guided gravel cycling holiday develops in the hilly and mountainous belt of Tuscany within the province of Siena, encroaching for a few kilometers in the province of Grosseto. It is a pleasure to ride in the realm of the most famous white roads, enjoying fantastic views over the historic villages, among grassy carpets, lively blooms, rural farms and the characteristic rows of cypresses. Definitely a varied tour from a historical - landscape point of view and with an excellent percentage of gravel, equal to 65%.


4 out of 5

The difficulty level of this Val d'Orcia Gravel Tour depends on 3 factors:

  • daily distances between 40 and 65 km (24,8 and 40,3 miles)
  • significant positive difference in height
  • gravel ground for most of the route

If you're a demanding traveller/cyclist and want to test your training on challenging terrains and ascents, you'll be fully satisfied. You'll be able to mix the training together with views and a complete cultural experience.


For our trips there is the possibility to rent Bombtrack Beyond 1 adventure bikes (sizes M and L) with complete equipment: classic bicycle tourism rack and panniers or bikepacking bags.
You can participate with your bicycle but, before leaving, check the characteristics of the trip and the type of terrain to be sure it is the most suitable vehicle.
We always recommend wearing a helmet. Its use is mandatory on guided tours.
Yes, when booking you can indicate your dietary needs and we will notify the facilities.
Yes, on request and subject to availability of the facilities, with a supplement.
Our Tour Operator has an agreement with the Axa insurance company and offers all its travelers a medical - luggage insurance included in the travel price. The information set of the policy can be consulted and downloaded at this link.
Yes, our Tour Operator makes available to its travelers, thanks to the Axa insurance company, a "Gold" insurance that covers the risks of trip cancellation and illness and injury during the trip even in cases related to Covid. The information set of the "Gold" policy can be consulted and downloaded at this link.
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The most complete solution for small groups of 6 to 12 people, a guided cycling holiday. A certified cycling guide from the Life in Travel team will lead you to discover the area. You will travel in the company of other people and we will be creating a close-knit and united group to have fun and share a unique experience that will remain imprinted in the memories for years.

What's included

- Certified cycling guide
- GPS track tested by Life in Travel
- Digital Guide of the itinerary
- Detailed information of the route
- 5 overnights in a 3 * or 4 * hotel in a double room
- 5 breakfasts at the hotel
- Luggage transport
- Medical baggage insurance (MB)

What's NOT included

- Dinners and lunches with drinks
- Double room single use supplement
- Possible tourist tax
- Experiences / museums / monuments entrances
- Adventure bike and accessories rental
- Travel Waiver Insurance (MBA)
- Anything else not specified in "What is included"

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