Due to the financial crisis that Greece has been facing in the last few years, there has been an ongoing dialogue on a regional and national level, based on studies, public forums, and consultations. Through this dialogue, the tourism sector has been identified as the main pillar of Greece’s economic development. As a result, a swift in the development strategy needs to be made to put emphasis on quality, competitiveness, innovation, and technological know-how on an international level. The main elements of this strategy is to connect tourism with the natural and cultural resources that Greece has to offer, the integration of new technologies on every aspect of the tourism sector, as well as the transfer of interest to the supply of a holistic experience for visitors. Based on these three elements, Pros-Eleusis (Personalized ROuteS in Eleusis) seeks to enhance entrepreneurship in the tourism and cultural sectors in Greece. The project aims to accomplish it by adopting an innovative approach in the tourist experience, the Ecomuseum approach, as well as offering a digital tool that provides personalized and dynamic tours. For the purposes of Pros-Eleusis, our approach will be implemented and tested in the city of Eleusis, the European Capital of Culture for 2021.