It is clear that concepts and cognitive processes aimed at putting forward fortified systems in their relation with the territory and with the surrounding landscape, establish inextricably interwoven “interests” and a consequent osmotic hysteresis between their emergence and disappearance into the deepest part of the earth. The logic behind the defensive structures of Euryalus fortress is particularly interesting. The fortress designed during the Greek period and located on the top of Epipolae hill, represented a strategic fortification for the city’s defence. Therefore, it is reasonable to think about a sequence of emerging or disappearing empty spaces; a semantic vacuum to be filled with logical-subjective interpretations pertaining to those who visit the place. The conceptual framework provides knowledge and documentation meant as indispensable supporting instruments to understand Dionysius I and Archimedes’ thoughts where the integration of people and environment forms the basis of the close iterative connection among nature, artifice and landscape. The research takes this direction implementing innovative technological systems trying to go beyond in order to achieve virtual reconstruction processes, even if partial, of the fortress. Survey, thus, can be applied as an instrument for the knowledge of historical heritage which once converted into digital heritage is a support for the reconstruction of lost ancient scenarios. Actually, the implementation of innovative systems allows an easy-to-use data viewing which supports the interpretive phase, the archiving, consultation and dissemination of survey products. In particular, the survey of the fortress with integrated methodologies (both instrumental and photogrammetric) provides not only a fundamental basis for the documentation of the fortress conditions but also provides a basis for the collection of reconstructive hypotheses formulated by researchers who have been involved with the structure so far. Interactions among archaeology, history, geomorphology and technology make history and a past renowned glory come alive with the common spirit of coming up to a strong synergy between the past and the future destiny of the place.