Internet of Things (IoT) technologies are widely recognized as key components of upcoming Smart Cities; however, pure technology is not sufficient for successful instantiation of the underlying vision of future urban settlements. Cities are mainly for humans, supporting their businesses, and involving the needed administrative entities. These existing stakeholders shall find new ways of interaction and new paradigms enabled by the IoT technological infrastructure to actually enact the full smart city vision. This chapter describes the steps along the tough and challenging path toward actual Smart Cities, pursued by ALMANAC (Reliable Smart Secure Internet Of Things For Smart Cities), an FP7-project cofunded by the seventh Framework Programme of the European Union.