This paper presents the case of an innovative national digital student competition for school groups of secondary education, entitled: “Hack the Art: Yanoulis Halepas.” Conducted remotely in Greece during the 2022 – 2023 school year, the competition was organized by the Onassis Foundation and the Onassis Library in partnership with the Teloglion Fine Arts Foundation, the National Gallery of Greece–Alexandros Soutsos Museum, the Cultural Foundation of Tinos, and the Cultural Center of Panormos-Municipality of Tinos. Accredited by the Hellenic Ministry for Education and Religious Affairs, it was realized under the aegis of the General Secretariat for Greeks Abroad and Public Diplomacy. This competition was the fourth iteration of this digital format since 2020. This time, we invited student teams from Greek high schools, both in Greece and abroad, led by at least one educator, to learn about the life and work of the great Greek sculptor Yanoulis Halepas and to communicate art by creating projects of augmented reality, virtual reality, digital storytelling, and 3D video games for PC and android devices. This innovative educational project enhanced students’ experience and conceptual understanding of art, motivating them to interact with cultural heritage and experiment with multimodal digital tools. Furthermore, it offered an alternative educational paradigm for teaching history, literature, visual arts, and technology by applying object-based learning, game-based learning, and project-based learning methodologies. According to the assessment results, this learning approach successfully integrated significant artworks into the school curriculum, extending their lifespan and visibility through digital transformations and reinterpretations.