Recent public cooperation between the Federal University of Technology Paraná and Toledo Municipality plans to implement the concept of smart cities in this city. In this context, one of the applications under development intends to track the recyclable garbage collector trucks in real time over the Internet. Actually, fleet vehicle tracking is one of the main applications for smart cities. LoRaWAN stands out among network technologies for smart cities due to operating in an open frequency range, covering long distances with low power consumption and low equipment cost. However, the coverage and performance of LoRaWAN is directly affected by both the environment and configuration parameters. In addition, tracking devices must be able to send its coordinates to the Internet even when the vehicle goes through zones where there are obstacles for electromagnetic waves, such as elevated buildings or valleys. In this paper we perform experimental investigations to evaluate four LoRaWAN tracking devices, two out of the box commercial and two assembled and programmed. The behavior of each tracking device is analyzed when moving through three representative urban areas. As the devices depend on the quality of the signal offered by the network, we also present the results of the development and evaluation of the LoRaWAN network, planning its coverage throughout the city. Results of tracking devices were analyzed under quantitative and qualitative aspects, including the received signal strength indication (RSSI), signal-to-noise ratio (SNR), package delivery ratio (PDR), and spreading factor (SF) for the geographic coordinates received.