The ongoing process of global urbanization has shifted the discourse from ‘developmental mechanistic’ towards ‘sustainable and ecological’ view. Global cities must also transition toward more dynamic, sustainable, healthier and smarter futures. However, the supportive transition theories, trajectory agendas, methodologies and pathways are currently under-investigated. This introductory paper provides an overview of the twenty-seven papers included in this special volume, with the objective to document the key lessons learned and to catalyze theoretical dialogue about the evolution of smart cities, healthy cities, eco-cities, and regenerative cities. These authors reviewed how these aspects of evolving cities are measured, monitored and implemented across different geographic, time and cultural contexts. After reviewing and mapping the obstacles and enablers in implementing transitions towards smarter, healthier, sustainable, regenerative, post-fossil carbon, urban societies, the authors of this introductory article provide insights into practical pathways and examples of best practices of their implementation in multiple social, cultural and climatic contexts.