Systems and methods are disclosed for generating a digital flight path within complex mission boundaries. In particular, in one or more embodiments, systems and methods generate flight legs that traverse a target site within mission boundaries. Moreover, one or more embodiments include systems and methods that utilize linking algorithms to connect the generated flight legs into a flight path. Moreover, one or more embodiments include systems and methods that generate a mission plan based on the flight path. In one or more embodiments, the generated mission plan enables a UAV to traverse a flight area within mission boundaries and capture aerial images with regard to the target site.