An electronic navigation system configured to receive a user's entry of calendar data of a planned event into an electronic calendar, including an indication of a point of time, a geographic location, and metadata descriptive of the planned event; enter the calendar data into a user specific trained classifier; process the calendar data by the user specific trained classifier to provide a classification result indicating whether a trip is required to participate in the planned event; if a trip is required, generate and send a request including the geographic location to a second server; generate navigation data including a predicted time duration for the trip, and return a response including the navigation data to the first server; generate and send a dynamic reminder message including the navigation data to the user's telecommunication device a variable amount of time before the planned event based on the predicted time duration.