In one embodiment of the present invention, a planning apparatus and method for earthmoving operations with a front-end loader, such as loading a bucket with material and unloading the material in a receptacle, is disclosed including multi-level processing for planning the operation. One of the processing levels is a coarse-level planner that uses geometry of the site and heuristics specified by expert operators to find an optimal area from which to remove material. The next level involves searching the area for an exact starting location. This is accomplished by choosing among candidate excavations for the site with the optimum performance criteria including maximum amount of material protruding from the pile, minimum side loading of the bucket, and minimum distance from the loading receptacle. Other performance criteria that are evaluated for the candidate excavation include whether the front-end loader is capable of making the turns required by a candidate trajectory, and whether obstacles are in the path of the trajectory.