Representative embodiments are directed to systems and methods for notifying a first party of an impending arrival of a second party. One of the systems comprises: a first data structure that identifies a plurality of sites that the second party is scheduled to visit that includes a predetermined location; a second data structure that defines when the first party is to receive notification of impending arrival of the second party; an interface process for receiving navigational data that is indicative of a location of the second party; a monitoring process that utilizes the navigational data and the first data structure to estimate arrival times associated with the plurality of sites; and a notification process that is operable in response to the monitoring process to generate a notification message for the first party to communicate the impending arrival of the first party according to the second data structure.