This paper develops new perspectives of cross-disciplinary methods combining futures studies and urban planning to help imagine healthier futures for compact urban cores. Our empirical basis lies in research-based collaboration between 2016 and 2019 with the City of Turku, the former capital of Finland. The goal was the creation of an ambitious but realistic vision and strategic plan focused on liveability and wellbeing and addressing challenges posed by spatial fragmentation and lack of cohesion. Through the process, it was concluded that to create a positive transition, planning requires the adoption of a ‘greensight’ perspective as a point of departure. The basic argument was that in order to reach a new level of human-centredness and interconnectedness, urban cores need to act as the strong support system for the healthier urban societies of the future. In this paper, we explain the lessons learned and provide an analysis of green areas in the context of Turku. We share wisdom on two key aspects: 1) the growing importance of human health for a more future-oriented approach to the planning of green areas and 2) the rising levels of urban complexity that make adequate distribution of green areas hard to achieve.