Uludağ / Mount Olympus is a mountainscape where natural and cultural values coexist. One of the under-researched cultural layers of Uludağ is the remains of the Byzantine Period monasteries, which are considered to compose one of the unique cultural landscapes of the Byzantine world. The site surveys realized by the Bursa Metropolitan Municipality Research Team proved that some remains still exist in the current Uludağ mountainscape. This study aims to understand the monasteries’ cultural landscape by integrating qualitative, quantitative, historical, and current data on the Uludağ monasteries in a Geographical Information Systems (GIS) model. Various analysis tools that GIS provides are utilized in order to estimate the approximate locations of the monasteries’ remains. In addition, the relationships of the monasteries with topography, city, and landscape are discussed through relevant GIS maps. As a result, it is observed that the Uludağ monasteries were located in hard-to-access locations and were well-integrated into nature. The cultural heritage of monasteries requires a multidisciplinary approach that can be managed by the utilization of GIS.