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Great Gravel Rides
Siena to Buonconvento
White gravel roads, medieval hilltop towns, and the Crete Senesi.
Distance
32 mi / 51 km
Elevation Gain
2,631 ft / 802 m
Best time to ride
Spring / Fall
Difficulty
Level 3
Every March, the world’s best gravel cyclists converge on Tuscany for Strade Bianche, a race whose name translates simply as white roads. The course threads through the rolling hills south of Siena on ancient unpaved lanes of pale gravel: the same roads that have connected Tuscan villages for centuries and that now form the backbone of one of cycling’s most celebrated one-day events. This route follows those same roads from the forests of Chianti through the medieval heart of Siena and south into the lunar quietness of the Crete Senesi, finishing in Buonconvento, a village whose name has been spoken by race commentators and cycling fans for decades.
Route Overview
The ride departs from Chianti and quickly joins the white gravel roads of the official Strade Bianche route, following the same course the professionals race in spring. Rolling hills carry you south through the Chianti forests before the terrain opens and the distinctive pale clay of the Crete Senesi appears on the horizon.
Siena arrives like a reward. The route weaves through its ancient narrow streets exactly as the race does, the stone buildings rising on either side, the lanes barely wide enough for a loaded gravel bike. A stop at the Piazza del Campo is mandatory. Note that cycling is not permitted in the square itself, so walk your bike and take the time to sit with a coffee and absorb one of the finest medieval piazzas in Europe.
South of Siena, the road turns wild. The Crete Senesi opens into a vast, strange landscape: pale clay hills rolling toward a wide sky, almost treeless, almost silent. It is one of those stretches of road where you stop thinking about effort and simply look. A pause in the shade of an ancient oak forest breaks the southern section before the route arrives in Buonconvento, a compact fortified village that has featured in the race’s defining moments and carries that history in its streets.
Interactive Map and Elevation Profile
Explore this route on a Gravel Bike Tour
If you’re inspired to experience this ride with expert support, curated hotels, and seamless logistics, explore the full Trek Travel itinerary.
Ride Highlights
- Ride the official Strade Bianche course Follow the same white gravel roads raced by the world’s best cyclists each spring and feel the character of the course from the saddle rather than the screen.
- The Crete Senesi One of the most distinctive landscapes in Italy: pale clay hills, wide open skies, and a profound quietness that makes the riding feel genuinely remote.
- Buonconvento and its cycling folklore Finish in a fortified village whose name is woven into Strade Bianche history, with the compact medieval streets and the satisfaction of having ridden the same roads as the race.
Frequently Asked Questions
How difficult is this ride?
This is a Level 3 route with approximately 50% on gravel and 50% on road. The terrain is predominantly rolling, with occasional punchy climbs up to Tuscany’s hilltop villages. The white gravel roads are firm and efficient when dry and require a little more care after rain. Learn more about gravel activity levels.
What is the terrain like on this route?
The route runs roughly 50% on white gravel roads and 50% on tarmac. The gravel sections are the firm, compact limestone-based roads characteristic of this part of Tuscany: fast when dry, requiring care when wet. The terrain is predominantly rolling with occasional punchy climbs up to the hilltop villages.
What should I pack for this ride?
Light layers are the priority for spring and fall riding in Tuscany. A packable rain jacket is worth carrying: the occasional shower can arrive without much warning, and the exposed sections of the Crete Senesi offer no shelter.
What is the best season to ride?
Spring and fall are both excellent. Spring is the classic season for Strade Bianche, with the race itself held in March and the Tuscan countryside at its most vivid green in the weeks either side. Fall brings softer light, harvest season in the vineyards, and cooler temperatures that suit the climbing well. See Trek Travel’s departure dates for this guided tour.
Where can I refuel along the route?
The main stop is a mid-morning coffee in Siena’s Piazza del Campo, one of the finest public spaces in Italy and well worth the pause. Sit with an espresso or cappuccino, take in the medieval architecture, and remember that cycling is not permitted in the square itself. Walk your bike and enjoy it properly. Buonconvento offers further options for a caffè on arrival, and the avid extension finishes with a wine tasting at the hotel estate in the Val d’Orcia.