Strade Bianche di Pienza e Montepulciano – round trip

Embark on a moderate 28.0-mile (45.0 km) racebike journey through Tuscany's Val d'Orcia, a UNESCO World Heritage Site. This round trip features 2749 feet (838 metres) of elevation gain and takes about 2 hours and 22 minutes to complete. You will navigate undulating Tuscan hills, cycling on a mix of paved roads and the famous unpaved gravel "strade bianche," passing through areas like the lunar-like Crete Senesi and cypress-lined avenues. Expect panoramic views and the chance to see picturesque medieval villages like Monticchiello and the Renaissance architecture of Pienza.

Be prepared for the unique terrain; the gravel roads, made of limestone, can be smooth in some parts but also rough with stones, especially after rain. While there are no single major ascents, the route includes numerous climbs, with gradients often reaching 8% and sometimes peaking at 15%. This trail requires good fitness, as the challenging gravel sectors involve constant ups and downs, and you might even need to push your bike in parts.

This route is more than just a ride; it is a deep cycling experience that combines physical demands with cultural immersion. The "strade bianche" are the namesake and inspiration for the professional Strade Bianche cycling race and the L'Eroica vintage bike race, making this region a pilgrimage for cycling enthusiasts. You can also explore historic towns like Montepulciano, enjoy local food and wine, and visit ancient cellars along the way.