Wayfinding, i.e. getting from some origin to a destination, is one of the prime everyday problems humans encounter. It has received a lot of attention in research and many (commercial) systems propose assistance in this task. We present an approach to route directions based on the idea to adapt route directions to route and environment's characteristics. The lack of such an adaptation is a major drawback of existing systems. Our approach is based on an information- and representation-theoretic analysis of routes and takes into account findings of behavioral research. The resulting systematics is the framework for the optimization process. We discuss the consequences of using an optimization process for generating route directions and outline its algorithmic realization.