Coastal areas and riverine cities accommodate the great majority of the world’s population, but they are extremely vulnerable to flooding risks. In the cities next to the Medway River estuary, the capacity to adapt to flood risks had been weakened by urban development and intense industrial usage. This degrading led to the loss of flood buffers and the recreational value of the coastal landscape. Moreover, climate change threatens large areas of nationally important habitats in the estuary. Coastal habitats are likely to be submerged by the rising sea. The rise in sea level can also accelerate the natural erosion of coastal cliffs. To address these problems, a more resilient landscape approach is needed to increase the coastal resilience. Therefore, this design-related research regarded resilience as the theoretical backbone, embraced landscape-based design approaches, including layer approach, scenario study, and mapping as research strategies. The project developed and applied design strategies in three lower-scale sites. First, the site on the Isle of Sheppey focused on coastline protection. A nature-based offshore island structure is proposed to diminish the surf, create space for tidal habitats, and provide recreational use. Next, on the Rainham coastline, to respond to intertidal habitat loss, managed realignment and growing marshes are the key strategies to restore the dynamics of the ecosystem. Last, the study proposed a transformation scheme for the Medway city estate site to relocate flood defence, provide space for tidal rivers, and accommodate mixed-use development. Each proposal could grow with time, increase ecological benefits, and create multifunctional programs. In the end, the study framed a vision on regional development, aiming to increase the socio-ecological resilience of the Medway river landscape.