A method and system for determining path plans to be followed by a fleet of agricultural working units during a harvest operation includes receiving a first set of input parameters related to a crop field and receiving a second set of input parameters related to an available fleet of working units. The fleet of working units includes a harvesting machine and a crop carting unit. A computer simulation of a harvest operation is executed based upon the first and second sets of input parameters. From the simulation, path plans are generated for at least two mobile working units.