In Chianti, cycling equals gravel because of the ubiquitous dirt tracks. L’Eroica, the best-known historic cycling event in the world, has made pedalling through verdant vineyards a must for bikers. Not that you need to be competitive to cycle these dusty trails and winding roads as permanent signposting means enthusiasts can take on these paths all year round. In technical terms, Chianti’s roads alternate gentle inclines with more demanding gradients (never more than 900 metres above sea level), doable for cyclists of all levels.
This picturesque bike route begins and ends in the town of Castelnuovo Berardenga, crisscrossing the four municipalities comprising the Siena province and Greve in Chianti in the Florence province. The 96-kilometre circular route is perfect for long-distance cyclists unafraid to take on challenging climbs. Road bikes are the best option here as we set off towards San Gusmè before the steepest of sections begins on the way up to the Monte Luco pass at 778 metres above sea level. A left turn grants us some respite as we drop down past Castagnoli and Meleto—park up your bike to peer inside the medieval castle with its ornately frescoed piano nobile, exquisite little theatre and age-old Chianti Classico cellars. Back in the saddle we take a right and ride to Gaiole in Chianti, the start and finish of the L’Eroica and the loveliest of towns to visit at any time of the year with its serene lifestyle. Next up, surrounded every which way by oak forests, is the ride up to 11th-century Badia a Coltibuono, once a monastery and now a renowned winery, hotel and restaurant if you’re feeling peckish. Back on the provincial road 408, a right turn calls for plenty of braking, followed by a final uphill stretch to reach picture-postcard Radda in Chianti—quench your thirst at Casa Chianti Classico, which details the region’s winemaking history. Ten kilometres separate Radda and Castellina before we start back south, skirting fortified Fonterutoli and Quercegrossa, where the natural springs will soothe your weary muscles. Approaching Siena, our final stretch leads us back to where we began.ù
Grit your teeth and go gravel along the L’Eroica route, even if you’re unable to make it to the annual October historic bike rally. Bring your own vintage velo and cycle the permanent route—it’s the perfect way of celebrating the beautiful fatigue of pedalling. Pick up your road book from any of the official outlets along the trail, gathering the six stamps as you cover the distance. In Chianti, start with a gentle climb that leads to Brolio Castle, the 12th-century redbrick castle owned by the Ricasoli family standing at the top of the winding, cypress-lined lane.
Brolio marks the beginning of your dirt track adventures through verdant vineyards and hillsides dotted with silver-green olive groves. The L’Eroica route crosses through Siena and the Val d’Arbia, Montalcino, the Val d’Orcia and Crete Senesi before returning to Castelnuovo Berardenga in Chianti. The way back along the road to Pianella offers varied scenery, switching between vines and woodland on the climb up to Vagliagli and Radda in Chianti before descending to Gaiole in Chianti, past the pretty village of Vertine.
The beauty of Chianti lies off these famous routes, however. From Radda to Volpaia, Figline Valdarno to Ama, Castellina to Monteriggioni, the gentle hills of the world-famous wine region welcome families and professional cyclists with short loops and challenging climbs.