The cabrei, or property books, of the Order of St John first appeared in the late sixteenth century. 1 These cabrei were of a juridical nature, being mostly a collection of notarial deeds, which dealt with the Order’s lands and buildings. By the mid-seventeenth century, the cabrei were more descriptive in specifying the Order’s territorial possessions. The cabreo changed into a descriptive manuscript used for legal purposes, recording the locations and boundaries of properties as well as their size, qualities and usage. 2 It was also during this period that drawn plans of these holdings started to appear in these cabrei. The agrimensore, or land surveyor, applied geometry to define a property’s given area and transform it into a two-dimensional drawing. This brought with it a methodical change in how space was perceived and represented from the Renaissance onwards. 3 This article will focus on the surveying process adopted by the Maltese agrimensore, from the geometrical surveys to the draughtsmanship of drawings, integral to the compilation of cabrei; a process which can be better understood within the context of surveying manuals which were available during this period. It will moreover compare and discuss analytically a number of drawn surveys from Malta’s cabrei.