An information processing apparatus includes a controller configured to execute the processing of finding, in connection with a first vehicle whose cabin unit and travel unit are separable from each other and that is scheduled to travel a first section of road in which travelling with a travel unit of a first type is suitable and provided with a travel unit of a second type different from the first type, a second vehicle that is scheduled to travel the first section in the direction opposite to the direction of travel of the first vehicle and finish travelling the first section and provided with a travel unit of the first type, and instructing the first vehicle and the second vehicle to exchange the travel unit of the first type and the travel unit of the second type.