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Multimodal journey planners have been introduced with the goal to provide travellers with itineraries involving two or more means of transportation to go from one location to another within a city. Most of them take into account user preferences, their habits and are able to notify travellers with real time traffic information, delays, schedules update, etc.. To make urban mobility more sustainable, the journey planners of the future must include: (1) techniques to generate journey alternatives that take into account not only user preferences and needs but also specific city challenges and local mobility operators resources; (2) agile development approaches to make the update of the models and information used by the journey planners a self-adaptive task; (3) techniques for the continuous journeys monitoring able to understand when a current journey is no longer valid and to propose alternatives. In this paper we present the experiences matured during the development of a complete solution for mobility planning based on model-driven engineering techniques. Mobility challenges, resources and remarks are modelled by corresponding languages, which in turn support the automated derivation of a smart journey planner. By means of the introduced automation, it has been possible to reduce the complexity of encoding journey planning policies and to make journey planners more flexible and responsive with respect to adaptation needs.