This paper reviews the results of an international expert workshop (SynCity2014), which searched for a new reading of the term “Smart City” paradigm from two specific perspectives: 1) creativity, 2) synchronisation of systems. On that background it compares creative smart city solutions for smart city logistics, public participation, urban simulations, and monitoring. Issues such as methodology, techniques, and instruments like multi-criteria analysis, multi-agent modelling, and technological foresight (backcasting) are presented and discussed.