This thesis takes on a combined approach, from societal and business development angles, to explore the question of ‘how to design for an active and healthy lifestyle. It follows a Research-through-Design approach, which generates new knowledge through the act of designing. A design-driven research method called Experiential Design Landscapes (EDLs) is developed together with accompanying tools and techniques. With the EDL method, the design process is taken into society by creating infrastructures where designers work together with stakeholders in jointly creating experienceable propositions that can evolve over time. These propositions, Experiential Probes, are intelligent, open, sensor- enhanced, and networked products service systems that enable people to develop new and emerging behaviours, and in parallel enable detailed analysis of the emerging data patterns by researchers and designers as a source of inspiration for the development of future systems.