This paper introduces a systemic approach that links public authorities (cities-regions) with private partners (e.g., banks, insurance companies and venture capitals) to cope with the disconnections and gaps related to the adoption of bankable transformative adaptation and mitigation measures. This is an important issue to face with climate change effects on civil infrastructures and towards resilience and sustainability of them against extreme phenomena. Starting from the Communities of Practice, we set up Living Labs, i.e., collaborative environments in which citizens, experts, and other stakeholders have the possibility to test and hone the methodology and the technologies. Innovative financing and investing schemes are tested and assessed for the adoption of the most promising bankable solutions. We follow already proven co-creation/design processes (including local communities), as well as the adoption and further adjustment of technologies that use data and collective intelligence to perform ex-ante simulation on-going and ex-post assessment in collaborative environments (digital twins and dashboards). By using Artificial Intelligence (AI)-based tools, a draft business model including a visual chart with elements describing the value proposition, infrastructure, customers, and financial elements of each investing scheme is generated, also identifying the best exploitation form based on the nature of the results and ownership structure (e.g., creation of spin-offs, products producing and selling, licensing of products/services, patenting, etc.). Once the best business model has been selected, a preliminary Business Plan is developed with the industrial partners being the main contributors. This business plan is beneficial for different stakeholders like public authorities, and insurance companies to cope with the impact of Climate Change (CC) on civil infrastructures.