Nature-Based Solutions (NBSs) are increasingly financed in urban, regional, and national contexts due to their proven capacity to reduce climate risks and deliver multiple co-benefits. Several challenges affect the successful implementation and long-term maintenance of NBSs, especially in climate-sensitive and fragile urban territories (e.g., the Mediterranean basin), characterized by intense urbanization, environmental vulnerability, socio-economic disparities, and fragmented governance. Key barriers include difficulties in economically evaluating NBS benefits, uncertainty about their effectiveness under changing climate conditions, and implementing multi-functional projects with an interdisciplinary perspective. To address these challenges, a participatory process was conducted involving three thematic working tables focused on the following: (1) economic evaluation, (2) co-design for climate resilience, and (3) multi-functionality and disciplinary integration. All groups applied a shared SWOT (Strengths, Weaknesses, Opportunities, Threats) methodology structured in four phases: (i) individual reflection and collective brainstorming; (ii) collaborative SWOT matrix development; (iii) roadmaps formulation; and (iv) narrative synthesis and submission. Grounded in their knowledge and practical experiences, stakeholders identified operational barriers and strategic advantages to identify research gaps and designing adaptive, inclusive, and context-sensitive NBS roadmaps. Although the stakeholders were primarily based in Northern Italy, they also brought national and international experience, making the findings relevant and transferable to other urban areas in the Mediterranean and Europe, facing similar socio-environmental challenges and governance issues. Thus, the study supports more effective planning and governance in comparable contexts, emphasizing integrated and flexible approaches to address urban fragility and optimize projects governance and management.