This paper presents preliminary investigations of two world heritage structures: Durham Castle in the UK and the dome of San Giorgio Church in Ragusa, Italy. These sites have been identified as pilot sites within the ongoing project “WRENCH – Whispers of Time: Heritage as Narratives of Climate Change”, funded by the Belmont Forum. The WRENCH project aims to evaluate the relationship between climate change, heritage, and local communities, using narratives to raise awareness of how climate change can affect the perception and use of heritage sites. The paper describes the initial steps critical to developing the knowledge phase. In particular, the historical analysis aimed at investigating the construction phases, modifications of the structural layout and use over the centuries, and the effects of past events on both the sites and the communities are described. This then served as the basis for digital surveys performed using laser scanners and UAV-based photogrammetry, experimental in-situ dynamic identification of the structures and preliminary identification of material characteristics through in-situ non-destructive tests. Furthermore, the paper shows the potential offered by the structural analysis approach not only in predicting the response of historic structures subjected to climate change but also in informing visual products fundamental to WRENCH’s targets.