A method of contextually displaying points of interest (POIs) on a personal navigation device according to a user's travel purpose includes storing a plurality of POIs into a memory of the personal navigation device, the POIs having corresponding POI category labels, entering a destination location into the personal navigation device and providing navigational instructions for a trip to the destination location, associating a travel category with the trip to the destination location, and displaying POIs whose corresponding POI category labels are included in the travel category associated with the trip to the destination location.