Many coastal communities worldwide are facing challenges caused by increasing sea levels. However, urban development, population growth and industrialisation in low-lying delta regions persist. This includes the Netherlands and British Columbia, Canada. Both regions explore new and innovative flood risk and adaptation strategies by initiating nature-based solutions (NBS) pilot projects and integrating research and community initiatives. The aim of this paper is to learn from the experiences with these NBS pilots and support practitioners with insights and knowledge about the prospectives and implementation process of NBS. Our study takes a bird's eye view by diving into four NBS case study projects that try to enhance flood defence and quality of life while considering ecosystems and community values simultaneously. To better understand current initiatives on NBS, we first describe the historical trajectories of flood risk management and climate adaptation policy in both countries. Then we analyse two urban and two suburban case studies to identify and compare enablers and barriers that surround the implementation of NBS. We use the Pilot Paradox as a framework to reflect on the enablers and barriers, and to formulate recommendations for barriers that are common ground. We found that upscaling of the pilots forms an important challenge in both countries. We also found that Canada is interested in exchanging technical knowledge, experiences, and insights with other countries through the involvement of international researchers, consultants, and students in projects. Such collaboration between countries, communities, practitioners, and academics could accelerate the development of innovative climate adaptation strategies worldwide.