During summer heatwaves, heat load exacerbates in urban heat islands (especially in hot climates) and threatens public life in cities. This paper examines the links between urban microclimates, outdoor thermal discomfort and public life through an exploratory case study. Heat resilience is highlighted as the ability of the space to support its normal activities when experiencing out-of-comfort temperatures. It also reports on the correlations between heat sensitive outdoor activities and urban greenery in three disparate case studies in Adelaide. Results indicate that necessary and optional activities start to decline after the apparent temperature reaches the threshold of 28 °C–32 °C, while activities in public spaces with more urban greenery show higher resilience to heat stress. Research findings propose heat resilience as a quality indicator in public space and support the application of urban greenery to make urban settings more resilient to heat stress.