An improved scheduling system for scheduling, in real time, two or more customer visits (e.g. pickups, deliveries, or service visits) in response to a single request. The single request preferably specifies a date and a time window for a first customer visit, and a periodic schedule according to which the customer visit should reoccur. Accordingly, the system allows a user to use a single request to schedule a series of periodically-reoccurring customer visits. In one embodiment, responsive to the request, the system firmly schedules the first customer visit, and tentatively schedules all other customer visits in the series. Shortly before each tentatively scheduled customer visit is to occur, the system determines whether to make the tentatively scheduled customer visit in view of holidays, capacity, and cost. If so, the system firmly schedules the customer visit. If not, the system notifies the user and allows the user to reschedule the visit.