As global urbanisation continues to increase, we need to understand how urban environments contribute to maintenance of public health across different geographic regions. Current public health and environmental psychology research to this end is geographically constrained, deficient in direct cross-cultural comparisons between populations. This exploratory study applies a standardised analysis framework to health and wellbeing metrics of cities in the UK, Sweden, Estonia, Kenya and Thailand. This allows for comparison between geographically diverse cities to understand their role on citizens’ health. We assessed demographics, subjective stress and wellbeing, relationships between green and public spaces and features of the local environment on health in 659 adult participants across six study locations. The results indicate regional differences in stress and wellbeing and show correlations with living close to, and engaging with, green and/or public spaces. Issues regarding noise, air pollution and traffic congestion were reported as having an impact on personal wellbeing. We discuss the impact that diverse properties of green space may have had, as well as cross-cultural considerations between the impacts of the local environments. This exploratory research provides a base for future cross-cultural research using mixed-methods and multi-disciplinary approaches to explore socio-economic and infrastructure dimensions of urban spaces and their impact on health and wellbeing.