This manuscript presents a multidisciplinary study that proposes a methodology for delineating and categorizing vulnerability at rockfall risk areas to avoid human injuries and infrastructure damage caused by rockfalls. The presented workflow includes (i) classical geological mapping, (ii) the interpretation of high-resolution satellite data for observing the spatial distribution of fallen boulders, (iii) analytical hierarchy processing of spatial information within a Geographical Information System (GIS) platform, (iv) close-range remote sensing campaigns with Unmanned Aerial Systems (UASs), and (v) integrated simulation of rockfall events. This methodology was applied to Kalymnos Island, which belongs to the Dodecanese Islands complex of the southeastern Aegean Sea in Greece. It is characterized by unique geomorphological features, including extensive vertical limestone cliffs that span the island. These cliffs make it one of the world’s most densely concentrated areas for sport climbing. The results highlighted the areas that the local authorities need to focus on and suggested measures for increasing the safety of climbers and infrastructure.