Based on a case study from Venezuela, the production of raw sugar is investigated. Ideally, sugar mills operate at a constant production rate. However, safety stocks of the raw material cannot be maintained as sugar cane quality deteriorates very rapidly. Sugar cane is therefore continuously sourced in diverse quantities and qualities from hundreds of geographically dispersed haciendas and supplied to the milling process. Furthermore, due to weather conditions changing throughout the year, tight time windows must be observed for harvesting. The approach presented in this paper aims at preserving a constant supply while minimizing the associated costs. The entire planning problem is structured in a hierarchical fashion: (1) cultivation of the haciendas, (2) harvesting, and (3) dispatching of the harvesting crews and equipment. The corresponding optimization models and solution procedures are introduced and applied to the case study problem.