An information processing apparatus, an information processing system, a vehicle, an information processing method and an information processing program which improve the utility of techniques for generating a travel plan for a vehicle are provided. An information processing apparatus includes a controller. The controller acquires first storage information indicating a stored amount of a first storage apparatus of a first vehicle provided with the first storage apparatus for storing drainage water. The controller generates a travel plan for a second vehicle provided with a second storage apparatus for storing the drainage water collected from the first vehicle, based on predetermined information which includes the first storage information.