The much-needed repair and rebuilding of Amsterdam’s historical quay walls and bridges coincides with growing demand for innovation, ranging from improved logistics and energy systems to enhanced biodiversity and climate resilience. These technology-driven transformations are unfolding in the heart of a World Heritage property known for its distinctive architectural and urban character. This article explores the complexities of integrating heritage into transdisciplinary design processes, focusing on the Canal Ring Area inside the Singelgracht. It proposes three axes for planning interventions that draw meaningfully on the past while addressing future needs, including those related to climate change. In particular, the article considers how historical analysis, spatial mapping and narrative-based approaches can strengthen the integration of historic spaces and practices into locally grounded, sustainable, climate-responsive design.