← All itineraries

Italy (Tuscany)

L'Eroica by motorcycle

Published on 24 February 2026

Distance
246 km
Calculated from the GPX track
Trip days
2–3
Difficulty
Easy/Moderate
Route type
Loop
Elevation gain
+4,180 m
Elevation loss
−4,180 m
Highest point
615 m
Lowest point
131 m

The route

A journey through the Tuscan hills, rich in history and beauty: white gravel roads and stone villages such as Gaiole in Chianti and Montalcino, for a slow-paced, authentic ride.

Country and region
Italy (Tuscany)
Road surface
Mostly gravel (15% asphalt, 85% unpaved)

Places and points of interest

  1. Gaiole in Chianti
  2. Montalcino

The story of the ride

L’Eroica by motorcycle is a journey where time stands still: a loop itinerary through the Tuscan hills, the gravel roads of Chianti and the Crete Senesi, stone villages, cypresses and vineyards. More than a route, it is a return to the roots of motorcycle travel, where true speed means enjoying a slow rhythm, the dry sound of the cylinders and the freedom of the road.

Gaiole in Chianti and Brolio Castle

Gaiole in Chianti is the first embrace: the square slowly waking up, the smell of coffee, motorcycles lined up next to old bicycles, as if time had decided to pause past and present.

A few kilometres on, Brolio Castle watches you from above. Here the gravel road narrows beneath its walls and invites you to slow down, as the sound of the cylinders blends with the rustle of the leaves.

Motorcycle on the gravel roads of L’Eroica in Tuscany

Gravel roads between Val d’Arbia and the Crete Senesi

Further south the villages become whispers among the hills. Between Val d’Arbia and the Crete Senesi you find tiny hamlets, stone houses and lonely bell towers rising from the fields like islands in a sea of rolling earth.

Radi, Murlo: names you may never have heard of, but that stay with you because of a half-open door, a cat in the sun, a silence broken only by your arrival.

Tuscan village along the L’Eroica motorcycle route
Tuscan hills and gravel roads by motorcycle

Montalcino and the way back through Radda, Vagliagli and Vertine

As you look out over the Val d’Orcia, Montalcino welcomes you with its fortress and narrow climbs.

The way back to Gaiole passes through more names that are a pleasure to say, Radda, Vagliagli and Vertine, each with a little square, a café, a low wall to rest your helmet on while your gaze drifts to the horizon. When you close the loop and switch off the engine, you realise that L’Eroica by motorcycle is more than a ride: it is a string of villages that, one after another, tell you the most authentic Tuscany.

Route map

Loading map…

Elevation profile

Partners & Gear

The gear for this trip

Insta360 logo

Insta360

Insta360 X5

360° footage up to 8K even in difficult light, FlowState stabilisation for smooth shots on the roughest roads, modes such as Pure Video and AdaptiveTone, and the invisible selfie stick for “drone-like” shots without a drone.

  • Collaboration
  • Used on my trips
  • Code provided by the brand