The analysis and assessment of European port cities are critical for effective urban planning and regeneration. This chapter emphasizes the need for a comprehensive knowledge model that integrates various disciplines to understand the complex dynamics between ports and their cities. By employing systematic methodologies and stakeholder-driven analyses, planners can identify existing challenges and opportunities, ensuring that urban transformations align with both economic and environmental goals. The discussion highlights the importance of mapping historical developments, assessing socio-economic trends, and leveraging data to inform strategic planning. Additionally, engaging diverse stakeholders, including vulnerable groups, is essential for fostering inclusive regeneration processes that enhance the resilience and vitality of port cities.