An automated vending system includes a physical item storage unit, and a plurality of land-based transportation mechanisms, or vehicles, arranged to store a predicted number and assortment of items to vend. A processing resource can communicate with the plurality of transportation vehicles, and is arranged to support a machine learning module. A plurality of data sources is arranged to provide data to the machine learning module to determine a plurality of respective actions for the plurality of transportation vehicles. The processing resource can communicate respective control instructions to the plurality of transportation vehicles. A selected transportation mechanism which receives the control instruction can operate in response to the control instruction in order to convey the item to a determined vending location.