This book presents a comprehensive examination of the complex interactions between port systems and urban environments, with a particular focus on international methodologies and site-specific case studies from the waterfronts of Palermo and Catania and the West Sicily Sea Authority. It addresses the multifaceted challenges and opportunities inherent in waterfront regeneration, emphasizing the critical importance of developing new urban interfaces that seamlessly connect ports to their surrounding cities. These interfaces serve not only as physical transitions but also as vital cultural and economic linkages that foster community engagement and enhance the liveability of urban spaces. The work offers a series of detailed analyses that highlight the necessity of integrating heritage protection within contemporary urban planning frameworks. By exploring historical developments and current initiatives, it provides valuable insights applicable to diverse global contexts, making it relevant for policymakers, urban planners, and scholars dedicated to understanding the future of port cities. Through rigorous exploration of strategic planning and stakeholder engagement, this book highlights pathways toward innovative solutions that respect historical contexts while advancing sustainable urban futures. By prioritizing the creation of effective urban interfaces, it contributes to the broader discourse on port-city relationships worldwide, underscoring their significance in shaping resilient and vibrant urban environments.