Unmanned aerial vehicles (UAVs), commonly known as drones, are being increasingly deployed throughout the globe as a means to streamline monitoring, inspection, mapping, and logistic routines. When dispatched on autonomous missions, drones require an intelligent decision-making system for trajectory planning and tour optimization. Given the limited capacity of their onboard batteries, a key design challenge is to ensure the underlying algorithms can efficiently optimize the mission objectives along with recharging operations during longhaul flights. With this in view, the present work undertakes a comprehensive study on automated tour management systems for an energy-constrained drone: (1) We construct a machine learning model that estimates the energy expenditure of typical multi-rotor drones while accounting for real-world aspects and extrinsic meteorological factors. (2) Leveraging this model, the joint program of flight mission planning and recharging optimization is formulated as a multi-criteria Asymmetric Traveling Salesman Problem (ATSP), wherein a drone seeks for the time-optimal energy-feasible tour that visits all the target sites and refuels whenever necessary. (3) We devise an efficient approximation algorithm with provable worst-case performance guarantees and implement it in a drone management system, which supports real-time flight path tracking and re-computation in dynamic environments. (4) The effectiveness and practicality of the proposed approach are validated through extensive numerical simulations as well as real-world experiments. Note to Practitioners-This study is stimulated by the need for developing pragmatic and provably efficient automated tour management systems for UAVs deployed on energy-constrained, long-distance flight missions. As such, UAVs provide a nifty platform for facilitating environmental monitoring, disaster management, transport of medical supplies, as well as expediting last-mile deliveries. However, existing path planners generally Manuscript