Since its original construction in 1573, the castle of Navarino (Niokastro Pylos, Greece) was periodically modified to suit the needs of its various inhabitants. The castle’s infrastructure consisted of buildings and streets that eventually fell into ruin, and is presently partially preserved.The case study below examines the different periodic stages of the castle of Navarino through the use of two technological methodologies in order to cross-reference data and create a well-rounded understanding of the site. Older maps of the castle were georeferenced, digitized, and visually compared to the site’s current condition through the results of GIS, generating a dialogue between the historic buildings, the existing buildings, and the paths from 1830 to-date. The use of technology in such research, based on mathematical precision, provides a visual understanding of the exact location of the buildings, their foundations, intact or collapsed, identifiable structures destroyed by human action, and verified pathways that existed within the walls of Niokastro as early as 1830. Furthermore, these digital maps recreate a completed image of the site and display how historic engineering influences the current state of the castle of Navarino, which will serve as a future guide for research, thus contributing substantially to the preservation of cultural heritage.