An online personalized gifting system and method includes an application executed on a computing device to communicate with a merchant server owned and managed by a merchant for generating customized gift structures that may be sent to a recipient. The application transmits the gift structure templates to a merchant server in communication with a user computing device, communicates with the merchant server to receive a selected one gift structure template that has been obtained by the merchant server from the user computing device, and communicate with the merchant server to receive at least one of user-supplied textual, audio, or video content that has been obtained by the merchant server from the user computing device. The application communicates with a production facility located at a site of the merchant to generate a gift structure in accordance with the selected gift structure template and the user-supplied content using a production facility.