Cities are living organisms with their physical infrastructure, habitants and visitors passing by. And intellectual events have a considerable impact on both physical and cultural transformation of these organisms. This does not only relate to the advertisement impact that the event creates, but deeper, is about how the event engages with the society and gives active roles to the local stakeholders. Training of the creative class through the right methodologies of entrepreneurship has a huge impact in co-creation of cultural values, and boosting the communication of the local potential. Goal of this paper is set on presenting a unique model of training for creative entrepreneurship, which also serves as a model for the local valorisation of cultural, creative and territorial resources. Within this framework, CREA summer academy is introduced as a European scale best practice case. Following this, the OSTUNI academy 2016 is unfolded as a symbolic model of site-specific event, which is able to generate entrepreneurship potential to valorise the cultural heritage. Summer Academy events, linking to the intellectual infrastructure of their location, are more beneficial to the territories when they have a strong link to the local stakeholders, as taken for granted by CREA Summer Academy.