This article focuses on the model of a sailing ship from the collection of the Maritime Museum in Orebić, Croatia, whose sails conceal material, visual, and symbolic enigmas that have raised a number of new research questions. Particular attention was paid to the analysis of the sail substrate material, which was previously incorrectly catalogued as leather, while research has revealed that it is, in fact, impregnated canvas. Prolonged exposure to inadequate storage conditions led to material deterioration and visible changes that severely compromised the visual integrity of the model. A synthesis of laboratory analyses, conservation, and restoration studies, as well as historical and archival research in an interdisciplinary framework, made it possible to identify materials and manufacturing techniques in detail. The painted decorations on the sails and flags become clearly legible after cleaning, providing new information about the ship’s name and royal affiliation and opening up new avenues for investigating the symbolism behind the motifs of this model.