Engaging university students into meaningful learning activities enables critical thinking and understanding (i.e. active learning), instead of memorising knowledge (i.e. passive learning). In this context, we researched the way students at the M.Sc. level learn, at the specialisation of Regional Planning and Development, in the Faculty of Geography, at Babeş-Bolyai University, in Cluj-Napoca, Romania. The aim of the activity was to discover the best means for students to analyse urban cultural landscapes. We offered them plenty of images (i.e. aerial photos) of a series of historical urban centres in Romania (ClujNapoca, Brașov, Sibiu, Oradea, Timişoara, Bistriţa) and, while working individually, we asked them to analyse the elements of the city centre and of the urban landscape: the features of the square, its arrangement, the features and the functions of the buildings. Students were also asked to use other sources of images (e.g. Google Earth, Google Maps, etc.) to complete the task, and then they used ArcGIS (a specialised software). In the end, we provided them with an observation protocol that they had to complete with the identified urban elements. We concluded that their in-depth analysis, enabled by an observation protocol, determined students' in-depth learning of the evolution characteristic of historical urban centres.