Tuscany Trail

The Tuscany Trail started as an annual bikepacking race and became the blueprint for Italian gravel adventure. The route runs from the outskirts of Florence south through the Chianti hills, the Crete Senesi, the Val d'Orcia, and the Maremma to finish near Grosseto on the Tyrrhenian coast. Every stage is different: the Chianti hills are green and demanding, the Crete Senesi has the lunar clay landscape that defines central Tuscany in photographs, and the Maremma is coastal scrub with the smell of the sea.

Strade bianche — white gravel roads — are the defining feature. These are not maintained surfaces. They drain poorly, wash out in rain, and turn the color of dirty milk in summer. They are also beautiful. The Val d'Orcia sections in particular look like every painting of rural Tuscany ever made, which is slightly surreal when you are in the middle of them.

The event runs annually in April-May but the route is rideable year-round in the right conditions. Spring is objectively the best: wildflowers, manageable temperatures, and the Chianti roads at their most photogenic. Late October is a close second. Summer is hot and the strade bianche are hard-packed and dusty — fine for riding, uncomfortable for camping.

Logistics are easy. Tuscany is not a remote destination. Towns appear every 15-25km through most of the route and accommodation ranges from agriturismo (the correct choice) to basic B&Bs. The food at every stop is excellent and the wine list does not require thought — order the local Chianti and move on.

The route is well-documented, with GPX tracks freely available.