The first detailed fiscal survey of Cyprus was recorded in the 1572 mufassal defteri, a year after the conquest of the island. Like any register of its kind, it provides important information in the economic structure of the Cypriot countryside, to the extent that this is reflected in fiscal data. The register includes 1,137 villages and settlements, recording the volume and value of taxable agricultural products, monetary taxes and dues for other sectors of the economy (manufacturing, salt pans, water management, etc.), and fines. While the data are more representative of the preceding Venetian rather than the Ottoman period, as well as concern a rather exceptional moment in that they record conditions on the island after a two year-long war, the register remains an important source for the study of the economy of the island. The paper presents the research outcomes of the “Mediterranean Insularities: MedIns”, project hosted at the Institute for Mediterranean Studies, Foundation for Research and Technology Hellas, in Greece. The project employed Historical GIS methods and tools for the purposes of geo-spatial and statistical analysis, and cartographic representation of the data recorded in the fiscal survey. It will discuss the limitations, challenges, and problems of using such methods, as well as the possibilities and prospects for future research.