Catania's waterfront regeneration presents a complex interplay between heritage protection and urban development, particularly in the context of its UNESCO-listed “Late Baroque Towns of the Val di Noto”. The area’s historical significance, shaped by the city's rich past and the challenges posed by modern infrastructure, necessitates a careful balance between transformation and preservation. The port, located at the mouth of the Amenano River, has undergone various phases of development and regeneration, yet it lacks a naturally sheltered harbour, complicating its relationship with the city. Recent initiatives, including the restoration of historic structures and the proposed railway bypass, aim to reconnect the port and city, fostering urban integration. However, barriers such as the “Archi della Marina” viaduct continue to hinder progress. The chapter emphasizes the need for coordinated efforts among stakeholders to create a vibrant waterfront that honours Catania's cultural heritage while enhancing urban quality and community engagement.