This paper provides a brief overview of, and elaborates on, some of the presentations, discussions and conclusions from Day 4 of the 'WHO EURO 2014 International Healthy Cities Conference: Health and the City - Urban Living in the 21st Century', held in Athens, Greece on 25 October 2014. The Internet of Things (IoT) is made of sensors and other components that connect our version of the world made of atoms, i.e., humans/our bodies, our devices, vehicles, roads, buildings, plants, animals, etc., with a mirror digital version made of bits. This enables cities and regions to be self-aware and dynamically reconfigurable in real- or near-real-time, based on changes that are continuously monitored and captured by sensors, similar to the way the internal biological systems of a living being operate and respond to their environment (homeostasis). Data collected by various IoT sensors and processed via appropriate analytics can also help predict the immediate future with reasonable accuracy, which enables better planned responses and mitigation actions. Cities and regions can thus become more adaptable and resilient in face of adversity. Furthermore, IoT can link atoms (humans) to other atoms (humans) (again via bits), resulting in the formation of 'smart(er) communities' that are socially connected in new ways and potentially happier. Cities, but also less urbanised regions and the countryside, could all benefit from, and harness the power of, IoT to improve the health, well-being and overall quality of life of the local populations, actively engage citizens in a smarter governance of their region, empower them to better care for one another, promote stronger social inclusion, and ensure a greener, sustainable and more enjoyable environment for all. Technology can also help reverse the 'brain drain' from the countryside and smaller towns to larger metropolises by making the former more attractive and connected, with better services akin to those found in larger cities. The article also discusses some ways of measuring and benchmarking the performance of smart cities and their impact on well-being. However, it should be emphasised that technology is not a panacea and that other factors are equally important in creating happier and healthier cities and regions.