The primary research topic of this article is to create and synchronize an updated “digital storytelling” experience using various web-based digital tools in Vocational Education lessons. We organize various digital tools, such as a virtual map-construction of web timelines-virtual exhibition with the “artstep” tool, and a website with the busts of many statues of Piraeus, depicting the evolution of the “numismatics” from Antiquity (from the “Tetradrachm”), until today (to “Bitcoin”). From the point of view of education, the target of this research is supporting teaching and learning for the Sector of “Financial and Administrative Services”–B’ class, and the four (4) specialties of Vocational Education and Training: “Administrative and Financial Services Officer”, “Warehouse and Supply Systems Clerk”, “Marketing and Advertising Officer”, and finally “Tourism Business Employee” C’ class. As a method, we used an interdisciplinary approach, the directions of the research concern all levels of education, from primary to secondary and up to Vocational Training Institutes. The interdisciplinarity of the subject involves the areas of History, Geography, Mathematics, Archaeology, Economic Theories, Sociology, Political Economy, and even Web and digital engineers (Engineers for Informatics and Electronic Engineers), from the point of construction view. Digital constructions will offer the educational community not only knowledge but also an occasion for discussion and analysis of the complex correlations that run through the economy of each period. The article as a result outlines the scientific framework of the constructs and concludes with proposed educational scenarios and future work of the working case.