Everyday travel in expanding cities is becoming increasingly complicated. Going to the doctor, to work, to the cinema, or simply discovering the districts of a city requires knowledge of the city and navigation skills. The future challenge is more than just providing correct guidance to make navigation easier; it is more about delivering the relevant information when it is needed and prioritizing the continuous development of the users’ navigation skills. This article aims to present a novel model based on existing literature about the cognitive wayfinding process by proposing a state diagram for interactive system analysis and design. This diagram may help to illustrate different states of the wayfinding task and how navigation aid systems for pedestrians can consider this context awareness to create an adaptive behavior considering the spatial knowledge of the user. A first study, focusing on one state of the wayfinding process: Path Following state, and its results are presented illustrating one example of different studies that can be designed considering our wayfinding model. At the end of this article, we highlight a set of design guidelines that may lead to the next generation of navigation aid systems based on the wayfinding model.