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 multi-destination trip planning in comparison to traditional information sources such as Google Transit. 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.