Urban heatwave is increasingly severe as the global warming advances. Even worse, especially in Japan, an increasing proportion of residences are vulnerable against heats under the aging society. Today, heatwave monitoring is an emergent task toward climate adaptive urban development. Our final goal is developing a smart navigation system to monitor real-time and micro-scale heatwave risk in Tokyo. To achieve it, we performed the following observation experiments: collection people location data with age information and people sentiment data by twitter, ground surface temperature monitoring by airborne and from the Tokyo Sky Tree. A method to combine these multi-scale information is developed to estimate micro-scale spatiotemporal behavior on heatwave risks. Based on the result, it is discussed how we can achieve the real-time and micro-scale heatwave monitoring, and make Tokyo more heat risk mitigative.