In 2018, 23.2 Mt of pears were produced in the world across 1.3 million hectares (ha) of cultivated land. This review analyzes different training systems and management styles that have been adopted worldwide, emphasizing the European pear’s economic and environmental sustainability for the Mediterranean area of cultivation. Despite a reduced number of cultivars utilized around the world, pear presents a plethora of innovative training systems. In Europe, dwarfing rootstocks have led to reduced planting distances and a subsequent increase in planting density. Still, the economic sustainability of these systems is now questionable. Many of the quince rootstocks have made it possible to considerably reduce the size of the tree and introduce the concept of continuous row planting, with the management of orchards from the ground (i.e., pedestrian orchard). The planting distance must be chosen according to the soil fertility, the vigor of the grafting combination, and the training system. The planting distance dramatically affects the pruning and the management of soil, fertilization, and irrigation. The reduction of tree size also lowers the volume of spray necessary when applying pesticides. The variability in yield worldwide results from the interaction amongst cultivar/rootstock/training system/climate/management.