The Piuro 1618 landslide represents a well-known case history of a large Alpine landslide. It destroyed the ancient village of Piuro (Italian Bregaglia Valley), renowned as an important trading center between the Mediterranean region and Northern Europe. The event had a significant impact among communities of all Alpine regions and was well documented by chronicles and paintings during subsequent decades. However, some aspects, such as the geometry reconstruction of the landslide body, the location of the landslide scarp, and its dynamics, remained undefined in previous studies, and a geomechanical characterization of the failure area is completely missing. Using field and laboratory analysis followed by stress–strain numerical modelling, this work develops a 3D conceptual geomechanical model of the slope considering its complex geological framework. The aim is to back-analyze the 1618 event, defining predisposing and triggering factors of the sliding event, and providing verifications on the geometry and location of the failure scar, as well as on the landslide dynamics. A coupled hydro-mechanical analysis with a 3D numerical approach is presented, assuming a rainfall scenario as a possible triggering factor. Simulated displacement and the development of a deep region of shear strain localization at a depth roughly corresponding to that of the detected Piuro sliding surface, allow us to highlight the mechanical role of geological elements outcropping along the slope and to validate the proposed scenario as a likely triggering factor for the 1618 event.