The paper deals with the interaction between freight flows, land use, and economy of a suburban area. In urban freight distribution, the process of freight acquisition of commercial establishments represents a crucial element. Therefore, it is necessary to plan city logistics in order to reduce the negative externalities generated by freight transport without depressing the economic and social vitality. In order to estimate and evaluate the performance and impacts generated by urban freight distribution, Transport System Models (TSMs) play an important role in reproducing and forecasting the process of distribution of final products to retailers and consumers. In recent years, Information and Communication Technologies (ICTs) have made new sources of data in great amounts available at lower costs than data provided from traditional surveys. Among the different data sources, Floating Car Data (FCD), obtained through GPS trackers installed on board the vehicles, offer partial insights into the examined process with lower cost and provide continuous information in space and time. In order to obtain reliable results, it is necessary to combine TSMs and ICTs as observed data could feed Transport System Models and could allow their calibration and therefore their application in real cases. In the above context, the paper deals with TSMs related to estimating urban freight demand flows. The work carried out concerns the specification-calibration-validation of a freight zonal acquisition model by means of FCD related to interzonal trips of commercial vehicles inside the Locride area (Reggio Calabria, Italy). The obtained models, estimated from FCD, could support the a priori evaluation of city logistics measures. The results are more important considering that they are obtained in an area with a lack of transport monitoring technologies. They could be adopted in other similar areas and confirm that adequate planning of city logistics determines advantages for environmental, social, and economic sustainability.