a b s t r a c tMonitoring, understanding and predicting city user behaviour (hottest places, trajectories, flows, etc.) is one the major topics in the context of Smart City management. People flow surveillance provides valuable information about city conditions, useful not only for monitoring and controlling the environmental conditions, but also to optimize the deliverying of city services (security, clean, transport,..). In this context, it is mandatory to develop methods and tools for assessing people behaviour in the city. This paper presents a methodology to instrument the city via the placement of Wi-Fi Access Points, AP, and to use them as sensors to capture and understand city user behaviour with a significant precision rate (the understanding of city user behaviour is concretized with the computing of heat-maps, origin destination matrices and predicting user density). The first issue is the positioning of Wi-Fi AP in the city, thus a comparative analyses have been conducted with respect to the real data (i.e., cab traces) of the city of San Francisco. Several different positioning methodologies of APs have been proposed and compared, to minimize the cost of AP installation with the aim of producing the best origin destination matrices. In a second phase, the methodology was adopted to select suitable AP in the city of Florence (Italy), with the aim of observing city users behaviour. The obtained instrumented Firenze Wi-Fi network collected data for 6 months. The data has been analysed with data mining techniques to infer similarity patterns in AP area and related time series. The resulting model has been validated and used for predicting the number of AP accesses that is also related to number of city users. The research work described in this paper has been conducted in the scope of the EC funded Horizon 2020 project Resolute ( http://www.resolute-eu.org ), for early warning and city resilience.