A Ride Through Cycling History: A Bike Tour on the Iconic Gravel Routes of Tuscany

Following the Tracks of Legends: Tuscany Calls to Gravel Cyclists

Italy has long been a place where cycling is more than a sport—it’s a way of life. From the alpine passes of the Giro d’Italia to the cobbled streets of ancient towns, the country reveres its two-wheeled heroes and the roads that made them. And nowhere is this cycling heritage more alive than in Tuscany.

Rolling hills, cypress-lined lanes, medieval hill towns, and sun-drenched vineyards make Tuscany a feast for the senses. But for cyclists, it offers something more: the iconic strade bianche—the white gravel roads that snake through the countryside like dusty threads stitching together centuries of rural life and racing history.

These roads are at the heart of two of the most storied gravel events in the world. The Strade Bianche, a modern professional race, challenges elite riders with steep climbs and loose gravel that turn every kilometer into a test of skill and resilience. Meanwhile, L’Eroica celebrates the romance of vintage cycling, inviting riders to don wool jerseys, ride steel-frame bikes, and honor the grit and glory of bygone eras as they retrace classic routes.

These events have helped transform Tuscany into a mecca for gravel cyclists. But you don’t need a race number to experience the magic. Inspired by these great traditions, we planned our own journey on two wheels—part pilgrimage, part adventure—through the timeless landscape of Tuscany. What follows is the story of that ride.