An improved automated tour guide system and method, intended to be run on mobile computerized devices such as Smartphone and GPS equipped vehicle devices, designed to better mimic the natural ability of human tour guides to customize tour guides according to variations in user interests and preferences, and tour itineraries, provide more natural segues between various tour stories, and more realistically handle what geographic regions of interest are visible to the user. The system extensively annotates tour guide media with control and preference metadata, can utilize third party media obtained from remote servers, and intelligently utilizes geographic map data and user location, movement direction, and speed to control tour guide audio, text, graphic and URL output to users. The system further keeps track of user tour location and media playback history and can use this history to further optimize its performance.