Planning and executing missions in terms of trajectory generation are challenging problems in the operational phase of unmanned aerial vehicles (UAVs) lifecycle. The growing adoption of UAVs in several civil applications requires the definition of precise procedures and tools to safely manage UAV missions that may involve flight over populated areas. The paper aims at providing a contribution toward the definition of a reliable environment, called FLIP (flight planner) for route planning and risk evaluation in the framework of mini- and micro-UAV missions over populated areas. The environment represents a decision support system (DSS) for UAV operators and other decision makers, like airports authorities and aviation agencies. A new ICT tool integrating an innovative procedure for evaluating the risk related to the use of UAV over populated areas is proposed.