Urban heat presents major health and well-being concerns with hotter, more frequent, intense, and longer-lasting heatwaves requiring urban planning and design approaches to prioritize heat mitigation and adaptation. The many benefits that urban greening in public space can deliver to address urban heat and create healthy livable places are well understood. However, the diversity of urban conditions, including climate zones, unique physical, social, and cultural characteristics, requires greening strategies to be tailored to specific contexts rather than adopting “generic” solutions. This chapter explores ways to first understand the heat-related attributes and vulnerabilities of a specific place before designing greening initiatives. The case study of an urban park renovation reveals that greening approaches can support healthy outdoor behaviors and highlights how to respond to heat-related contextual factors and microclimatic conditions, and work with communities to design and implement green interventions for cooler public spaces.