This travel-based research project focuses on the transformation of four coastal cities located along the Straits of Malacca. This project is neither a comprehensive study of port cities, nor it is detailed on a thorough historiography of coastal cities in Singapore and Malaysia. Instead, it undertakes architectural survey to explore the recent waterfront developments along the Straits of Malacca. Looking at these four historic entrepôts - Penang, Malacca, Singapore and South Johor, the four selected sites of study show a continual and dynamic impetus of waterfront imagination. The case studies of invite us to reflect on the changing uses, meanings and identities of waterfront spaces across different localities. Indeed, they transcended the legacy of colonial past, and continue to be primarily their own city transformation.