Abstract: A trip planning and reservation system and method is disclosed that may include a U.I. software application executing on a computing device (e.g., mobile device). The U.I. software application may transmit the user account information to an external server. The external server may validate the user account information and transmit an access token to the mobile device. An AI algorithm may be operable to predict and select the plurality of digital media files based on operational data that includes the user account information and one or more user interest tags. It is contemplated that the digital media files may include geographic coordinate data and informational data about a location within a pre-defined proximity of the desired travel route. A first file may then be selected from the plurality of digital media files for inclusion within the desired travel route displayed by the U.I. software application.