Modern cities are intrinsically multidisciplinary and multicultural places. Inspired by that view, this chapter has invited a cross-disciplinary international team of domain experts to present their differing views (in their distinctive styles) on the current state and future evolution of smart cities. In presenting their views, the experts have adopted the metaphor of a journey, since the people, organizations, and technologies comprising a smart city can be regarded as being on journeys from conception to death, from start-up to bankruptcy, and from innovation to obsolescence. To do this, the chapter begins with a person-centric exploration of smart cities, examining topics such as innovation, entrepreneurship, generational issues, memory, and education before ending with a set of discussions around the key enabling technologies such as artificial intelligence, the Internet of Things, smart transport, mixed reality, and wearables. The chapter concludes by regarding the smart city as a type living laboratory for innovative technology development, reflecting on the expert’s opinions for potential directions of travel that smart city research might take.