This paper presents a smart city pilot project that will be developed in the city of Bologna. Different sensor devices will be deployed in several buildings to measure environmental quantities, such as temperature, humidity, luminosity and CO2. The pilot will use the LoRa low-rate, long-range communication technology to transmit sensed data to the control center. Results of a measurement campaign to characterize the propagation in the Bologna scenario are reported. Such results are then used as input to a simulator that provides both coverage and networklevel performance of the LoRa technology in the considered scenario. The paper shows that a proper parameter setting is needed to cover large urban areas while maintaining the timeon- air sufficiently low to keep packet losses at satisfactory levels.