According to the current European and Italian scenario related to urban re-generation, cultural and landscape heritage, valorisation is being also enhanced by the activation of innovative processes. These involve the development of methodologies and tools that are able to address decision-making processes among low entropy economy, complex values and creative practices. In this perspective, the research aims to investigate the possibilities of developing a Cultural Heritage Low Entropy Enhancement (CHLEE) approach by considering how the complex values of cultural heritage can vary not only through a physical transformation of spaces but also through a program of uses and activities able to produce new values, where the human experience is essential. This type of model modifies the objectives that characterise the valorisation of cultural heritage and landscape, recognising that the fruition is no longer “consumerist” but “experiential”. A crucial role is represented by the heterogeneity of creative practices that contribute to the identificationidentifying and implementation ofimplementing innovative management and governance models. The present paper explores the components of creative regenerative processes, based upon the ex-post evaluation of some Italian experiments, across the PROMETHEE-GAIA multi-criteria method, to understand how creative experiences are building innovation ecosystem thanks to low entropy economy and improve the ex-ante evaluation for new strategies and policies.