A server manages operation of a plurality of vehicles that are autonomous and used for transporting a plurality of users. The server includes a server communication interface and a server controller. The server communication interface is configured to be able to transmit/receive information to/from the plurality of vehicles. The server controller is configured to be able to transmit, via the server communication interface, an instruction to couple a first vehicle and a second vehicle which are included in the plurality of vehicles to thereby form a vehicle group which includes the first vehicle and the second vehicle in a coupled state, and control the first vehicle and the second vehicle so that a user in either one vehicle of the first vehicle and the second vehicle can move to another vehicle, and an instruction to release at least part of the coupled state of the vehicle group.