Nowadays the natural environment as well as the urban environment undergo a permanent alteration, under the pressure of residential and touristic development combined with the prospect of increasing profit for different social groups at a global level, a process which the state apparatus is often unable to control and restrain. In this context, a system for remotely monitoring cultural heritage assets, whether buried, excavated or still standing, of various time periods, as well as for drawing up public projects and national strategy, should be considered as an urgent need. Hence, observing the earth’s surface for detecting and locating traces of cultural activity and mankind’s artifacts, by applying remotely sensed imagery’s photointerpretation, could be considered as the most effective procedure in the perspective of restoring our cultural past. Gathering extensive documentation of various types of data, bibliographic, archaeological, geospatial and optical, of multiple dates, inserting and comparatively studying all the components in a GIS environment, can lead to the extraction of qualitative and quantitative data, which in turn may constitute irrefutable witnesses of relics, whether visible or not, of our cultural course. The specific paper focuses on two different case studies: the first one, on the plateau of the northern arm of Voidokilia bay, Peloponnese, a natural landscape under a NATURA protective framework, uninhabited in modern times, ending up in locating buried archaeological relics of the prehistoric period; the second one, on the contemporary city of Ioannina, Epirus, an urban landscape, ending up in locating destroyed architectural assets (landmarks) of the historic period within the dense urban web of modern times. In both cases the cultural relics’ qualitative and quantitative documentation has been achieved. Both sites are located in Greece.