Public transport travelers require well-integrated, real-time information systems to use a network. The objective of this study was twofold: (1) to develop a model to determine the effect of personalized information provision through smartphones on user ability to plan multi-destination trips, and (2) to understand user perception of riding public transport aided by real-time, multi-destination trip-planning smartphone applications. Auckland Pioneer was developed for multi-destination trip planning and integrates real-time public transport services with search functions for places of interest. A test trial was conducted in Auckland, New Zealand, and the findings show the effects of the application on multidestination trip planning in comparison to traditional information sources such as GoogleTransit. This research contributes to existing literature by demonstrating the importance of personalized information en-route for user multi-destination trip planning. With information to assist trip planning and provide step-by-step guidance en-route, users tend to feel more confident to ride public transport.