Tuscany Gravel Weekend between historic villages and hills planted with vineyards. Start your self guided gravel bike tour in the amazing setting of Val d'Orcia on the world's most know white roads.

Brunello Gravel

139,00 € p.p.
Self Guided Tour
Duration 2 days

Adventure Bike
Single room supplement


Brunello Gravel Weekend is a Tuscany bike tour in the lands of Siena, the renowned Val d'Orcia, the gentle hills furrowed by white roads, the rows of cypress trees and the typical vineyards of wine-growing areas of absolute value. During the two days of this gravel bike tour in Italy you will have the opportunity to discover new territories and taste the gastronomic delicacies typical of Tuscany accompanied by a tasteful glass of Brunello D.O.C.G. You will ride through medieval villages breathing in the rural culture that has made this land unique in the world; you will travel along dirt roads between farms and breathtaking views in a valley registered in the World Heritage sites.

Stage by stage


Brunello Gravel is a 110 km (68 miles) bike tour that develops in the province of Siena along the characteristic white roads of Tuscany. Its ring configuration allows you to travel along the most beautiful gravel roads in the region, passing through historic villages, farms and vines of the finest Tuscan wines.

1st stage: San Quirico d'Orcia – Montalcino

(55 km 1500m D+: paved 45%; gravel 55%)(34 miles 4921 feet elevation gain)

From the Horti Leonini of San Quirico d'Orcia we head towards the hilly area that anticipates the entrance to the valuable historic center of Pienza. After passing the town, from which you can enjoy a fantastic view of the Val d'Orcia, you cycle towards the ancient Roman baths of Bagno Vignoni until you reach the imposing Rocca Tentennano adjacent to Castiglione d’Orcia. Continuing along pleasant dirt paths you reach the imposing Abbey of Sant'Antimo before ending the day in Montalcino.

2nd stage: Montalcino – San Quirico d'Orcia

(55 km 800m D+: paved 40%; gravel 60%)(34 miles 2624 feet elevation gain)

The second day of the trip is dedicated to the discovery of ever new and stimulating places and landscapes. Once you have crossed the town of Montalcino, on whose hills the prized Brunello di Montalcino is produced, you head towards Buonconvento pedaling along the fantastic permanent route of l'Eroica. Among castles and museums, cypresses and unforgettable sunsets, this exciting ring tour on pedals ends in San Quirico d’Orcia.

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Brunello Gravel Bike Tour

and its hills

Spectacular weekend on Tuscany's most known Strade Bianche, riding and tasting wine

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  • The historic centre and UNESCO site of Pienza
  • Strade Bianche and the permanent route of l'Eroica by bicycle
  • Finocchiona and Brunello D.O.C.G., Cantucci and Vinsanto
  • The majestic Abbey of Sant' Antimo
  • Following Sigeric's Via Francigena
  • Bagno Vignoni and the ancient Roman baths
  • The rows of cypresses along the Val d'Orcia


The overnight stay is provided in a 3* or 4* hotel in Montalcino in a double room with private facilities. If the facilities are not available, we will guarantee alternative accommodation of the same level in a location not far away.

Type of terrain

The itinerary develops in the hilly area of ​​Tuscany within the province of Siena. Immerse yourself in the realm of the most famous gravel roads and tours in the world, enjoying incredible views of the historic villages and the gentle slopes planted with vineyards. This tour offers a 360-degree experience embracing history, landscape and local gastronomy, with an excellent percentage of gravel, equal to about 60%.


    4 out of 5

The difficulty level of this Brunello Gravel Weekend Cycling Tour depends on 3 factors:
  • daily distances of 55 km (34 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 with this bikepacking weekend. 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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A bikepacking trip with your partner, family, friends or simply alone will be the most authentic way to experience an unforgettable experience. While we will take care of the bureaucratic and organizational management, you will only have to think about having fun and spending your cycling holidays in tranquillity.

What's included

- GPS track tested by Life in Travel
- Digital Guide of the itinerary
- Detailed information of the route
- Telephone / Whatsapp assistance
- Overnight in a 3 * or 4 * hotel in a double room
- Breakfast at the hotel
- Medical Baggage insurance (MB)

What's NOT included

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

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