An excavation system is disclosed as having a locating device configured to generate a position signal indicative of a position of an excavation machine, a sensor configured to generate a load signal indicative of a work tool status, and a controller. The controller may be configured to determine a location of a haul truck, to determine when the work tool is filled with at least a threshold amount of material from a pile at the worksite, and to determine the position of the excavation machine. The controller may further be configured, based on operating limitations of the excavation machine, to determine a pivot point between the location of the haul truck and the position of the excavation machine; to plan a travel path for the excavation machine to the haul truck through the pivot point; and to direct an operator of the excavation machine to follow the travel path.