A method is described for incorporating a new waypoint into a current trip. The method includes configuring a trip definition and thereafter determining a proposed POI based upon: the trip definition, and a collection of potential proposed POI instances. The waypoint server system processes the collection of potential proposed POI instances, to render the proposed POI, by: (1) establishing POI ratings for individual ones of the collection of potential proposed POI instances based at least in part upon: the delay factor, and an estimate of additional delay arising from adding the individual POI to the current trip route; (2) establishing a rank ordering of the individual ones of the collection of potential proposed POI instances based upon the POI ratings; and (3) rendering the proposed POI from the rank ordering of the individual ones of the collection of potential proposed POI instances.