Val d’Orcia Walking Holidays

This route takes you through one of Tuscany’s most recognisable rural landscapes, where white roads cross open hills between vineyards, cypress ridges and Renaissance towns. The Val d’Orcia has long been associated with farming, wine and food, and the walking gives you time to experience that slowly.

There is plenty to pause for along the way: a view back to Pienza, the approach to Montalcino, or an evening meal built around local produce. The area is known for Brunello wine and pecorino, with seasonal festivals celebrating local food and wine.

The valley takes its name from the River Orcia, and its wide views have been painted, photographed and revisited for centuries. On foot, though, the pleasure is simpler: steady days through countryside that still feels worked, lived-in and rooted in place.

The distances between places feel part of the experience, not just the space between stops. White roads, working vineyards, abbey churches and hill towns sit close enough together to make the route feel natural from one day to the next.