The educational philosophy of the 21st century focuses on three pedagogical principles: Personalization, participation, and productivity. In our digital era, cutting-edge technologies support the application of those principles as learners face new challenges, but at the same time, they are presented with new learning opportunities. In order to adapt, learners need to move away from passive learning techniques and discover how to apply critical thinking, communication, collaboration, and creativity within the learning process. These skills are often referred to as “the 4Cs”. When young people play online games, peer-to-peer collaboration is encouraged. When they actively participate and contribute their thoughts in Web discussions, they actually evaluate the content and when other users decide to share and publish their content, they become “prosumers” (both consumers and producers) supporting this very important cycle of content creation. The dynamics of new interactive media support personal meaningful learning through collaboration, social interaction, and shared knowledge building. In this work, a cultural heritage-oriented case study is presented in which we concentrate on contemporary transmedia learning approaches that enable learners to engage in formal and informal learning environments, assume control of the process, and interactively focus on aspects that cover their personal interests.