This book provides an interdisciplinary lens for exploring, assessing, and coming to new understandings of smart cities and regions, focusing on the six dimensions of sensing, awareness, learning, openness, innovation, and disruption. Using a hybrid case study and correlational approach, people from diverse sectors in a variety of small to medium to large-sized cities in multiple countries (e.g., Canada, United States, Ireland, Greece, Israel, etc.) provide experience-based perspectives on smart cities together with assessments for elements pertaining to each of the six dimensions. The analysis of findings in this work surfaces a rich and interwoven tapestry of patterns from the qualitative data highlighting for example, the importance of emotion/affect, privacy, trust, and data visualizations in influencing and informing the directions of smart cities and regions going forward. Correlational analysis of quantitative data reveals the presence and strength of emerging relationships among elements assessed, shedding light on factors that may serve as starting points for understanding what is contributing to potentials for improving success in smart cities and regions.