In recent years, the concept of a “Smart City” became central in the agenda of researchers, practitioners, and stakeholders. Although the application of information and communication technologies on city management has advanced exponentially, also other components would be needed for building a truly sustainable urban environment. Researchers from different domains debated the definition of a smart city and the conceptual variants. However, a broad view of the smart city field is still missing. This paper attempts to fill this gap by proposing a taxonomic classification of the most 105 outstanding smart city projects in Europe and North America. Collected data are then processed by statistical tools for clearly highlighting the success factors, trends and future paths in which all these projects are moving, along with different aspects (e.g., business model, purpose, industry). We then investigate the European and the North American Smart City concepts, illustrating the key role of mixed public and private partnerships in creating successful projects and the focus on the urban transportation, and freight and last-mile delivery in particular. Moreover, it emerges how the business modeling and the exploitation aspects have still low integration in the projects.