Cultural heritage is considered a resource for local sustainable development, although there are some contradictions. The sites recognized as cultural heritage are increasing; the costs for functional maintenance/reuse are growing, while public resources available are becoming scarcer, and private actors are increasingly focused on the short time for payback. The consequence is that there is a growing risk that the decay of heritage increases year by year, because of lack of funding support and viable business models. This is the context of CLIC trans-disciplinary research project whose overarching goal is to identify evaluation tools to test, implement, validate and share innovative “circular” financing, business and governance models for systemic adaptive reuse of cultural heritage and landscape, demonstrating the economic, social, environmental convenience, in terms of long lasting economic, cultural and environmental wealth.