Tuscany Gravel Adventure: On the Trail of Strade Bianche | Epic Gravel Bike Tour

Leaving the UNESCO Heritage town of Siena, you quickly join the official Eroica route and sample your first stretch of white gravel at Montechiaro. Next, the Pianella uphill gravel sector rewards you with panoramic views over Chianti’s rolling vineyards. A paved climb brings you to Radda in Chianti, a medieval village with breathtaking vistas of the Val di Pesa. One last stretch of white road descends into Gaiole, where your stunning accommodations await. A perfect start to your Tuscany gravel adventure.

This is a day to explore in more depth the rugged Chianti Classico region between Florence and Siena. Heading North out of Gaiole, the longer option visits the charming hilltop towns of Panzano in Chianti and Radda on a spectacular and challenging gravel circuit. A shorter version of this loop with less climbing visits Radda and the ancient walled village of Volpaia.

Departing from Gaiole, your route rejoins the official Eroica path, leading to one of Tuscany’s most iconic landmarks: Brolio Castle. A stop at the Eroica Café provides a welcome energy boost for the final gravel climb to the castle. After conquering this challenge, continue through the charming town of Castelnuovo Berardenga before tackling the spectacular and demanding Monte Sante Marie gravel sector, featured in both the Eroica and Strade Bianche races. Your day concludes in historic Asciano, the largest town in the Crete Senesi, where you can enjoy a well-earned meal in one of the regional restaurants.

After a gentle start on paved roads, the gravel returns as you pass through Buonconvento and enter the stunning Val d’Orcia. Ride steadily uphill through Lucignano d’Asso, an olive oil town set along some of the most breathtaking white roads in Tuscany. A final paved stretch leads to the UNESCO Heritage site of Pienza.

If your legs allow, take a detour to visit the renowned wine town of Montepulciano before tackling the final climb into Pienza. Spend the evening wandering this enchanting hilltop town and soaking in its panoramic Tuscan vistas.

A spectacular day of gravel riding is on offer today that includes a visit to the fabled wine village of Montepulciano. The ride starts with a gentle downhill on paved roads before turning to gravel and passing through Montefollonico. Next, an uphill into hilltop Montepulciano rewards with spectacular views of the famous wine area. The loop continues through Monticchiello for the final awe inspiring stretch back into Pienza along the cypress-lined gravel road made famous by the movie Gladiator. A slightly longer loop joins the Francigena cycling path for a bit and passes the Spedaletto Castle before rejoining the 'Gladiator' road back into Pienza.

For your triumphant return to Siena, you’ll ride exceptional gravel roads through some of the most well-known sectors of Tuscan gravel riding. Shortly after leaving Pienza, the first gravel stretch winds through the rolling hills of Crete Senesi. It connects with the historic Via Francigena pilgrimage route, leading to the UNESCO Heritage town of San Quirico d’Orcia. Continue along gravel tracks through the vineyards of Brunello di Montalcino before arriving in Buonconvento.

For those ready for a challenge, a detour up to the town of Montalcino provides a fantastic panorama of the area before descending and rejoining the main route before Buonconvento. The home stretch follows the Strada Bianca Murlo–Siena, a celebrated sector of both the Eroica and Strade Bianche. The final uphill climb brings you back into Siena and the iconic Piazza del Campo—an unforgettable finish to a true Tuscan gravel adventure. Check into your hotel and savour the satisfaction of completing this epic loop.

After an early breakfast, enjoy a relaxed morning in Siena to wander its medieval streets, sip a final cappuccino in Piazza del Campo. A transfer to Florence airport concludes this unforgettable Tuscany gravel bike tour. Or stay in Siena for further explorations.