The purpose of this research is to improve an understanding of travellers as users of mobile travel applications (apps). Research was conducted on travel motives, mapping and navigation-related technology, as well as mobile travel app attributes to find the best design and performance solutions for user engagement. Secondary research and a competitive analysis of current mobile travel apps was performed to rate the effectiveness of app interfaces. Using these findings as a guide, it proposes an interactive self-guided travel app under the title DROP/PIN. DROP/PIN allows travellers to explore urban environments in real-time through personalized interests, big data, instant messaging and navigational technology. Through this implementation, a prototype of the app was created. DROP/PIN aims to foster a traveller’s digital identity through constant personalization and data recognition, social interactions by profile compatibility, and a common interest in global exploration.