A network system for serving digital content to a graphical user interface of a user device is provided. The system includes a database storing user data including user preferences and events in a calendar of a system user; a processor configured to automatically scan the database to determine an event scheduled for a predetermined window of time; to automatically determine the event is associated with travel by the user and access one or more travel services, and to prepare content conveying a travel package customized to the event of the user; and a server to serve the content for presentation by the graphical user interface.