A method for generating a customized travel itinerary is disclosed. The method may comprise associating an individual with a travel sign based upon the results of a travel quiz; associating the individual with a travel location based upon the travel sign and a travel date; and associating the individual with an activity item based upon the travel sign. The method may additionally comprise receiving, by a mobile communication device, a travel itinerary comprising a plurality of travel locations; displaying, by the mobile communication device, a first travel location from the plurality of travel locations prior to a scheduled departure time for the first travel location; and displaying, by the mobile communication device, a second travel location from the plurality of travel locations prior to a scheduled departure time for the second travel location.