Actively encouraging foreign language learners to establish a meaningful connection with the target language culture--by engaging in authentic activities with other learners and native speakers in real-world communicative contexts--is a critical goal of foreign language education. This paper describes a design-based research study that investigated how students of Italian at an Australian university engaged with and responded to a webbased learning environment which integrated authentic learning tasks to facilitate social interaction and meaningful collaborative language practice with native speakers of the target language. The findings suggest that the use of the critical elements of authentic activities actively supported student learning across different domains. A major outcome of this research was the development of a set of design principles and guidelines for the design and development of authentic foreign language learning environments that could inform and guide other language educators within their specific educational context.