An information processing system includes one or more vehicles; and a server configured to communicate with the one or more vehicles, wherein each of the one or more vehicles is configured to generate a first video of a traveling route by capturing an outside scene while traveling, and the server is configured to store a plurality of the first videos generated by the one or more vehicles, generate a second video of a specific route using two or more of the first videos, the specific route being different from the traveling route of each of the plurality of the first videos, and send the second video to a terminal device.