A transportation system includes a traveling route, vehicles, and a service management device. The service management device includes a timetable generator that generates a timetable for each of the vehicles, and a communication device that is configured to receive passenger information at least from the vehicles or stops. The timetable generator calculates a boarding and alighting time estimate of the vehicle at the stop based on at least the passenger information such that a higher average speed of the vehicle between the stops and a longer dwell time of the vehicle at the stop are set for a longer boarding and alighting time estimate.