A smart city is a high-performance urban context, where citizens are more aware of, and more integrated into the city life, thanks to an intelligent city information system. In this paper we design, implement and deploy a smart application that retrieves and conveys to the user relevant information on the user’s surroundings. This case study application let us discuss the challenges involved in creating a location-aware mobile service based on live information coming from the city IT infrastructure. The service, that is currently being deployed in the Italian city of Cesena, has been designed with the goal of being a general model for future applications. In particular, we discuss location-aware and mobile development, cloud and cluster based geographical data storage, and spatial data computation. For each of these topics we provide implementation and deployment solutions based on currently available technology. In particular we propose an architecture based on a complex On-Line Transaction Processing (OLTP) infrastructure. Furthermore, this paper represents the first comprehensive, scientific study on the subject.