Text visualisations provide visual representations of documents or small corpora with the primary aim of supporting language analysis. We are interested in developing a more playful approach to language that can be characterised by the notion of wandering as an open-ended movement. To support such a casual form of engagement with text, we designed the WordWanderer system: a visualisation technique that extends tag clouds into a navigational interface for text. The tool supports the gradual movement between word ‘context views’, which represent the words that co-occur in the vicinity of the selected word, and word-‘comparison views’, which arrange words based on their association strengths between two selected words. We report on the encouraging feedback from a ten-day deployment of the interface and present promising directions for future design and research.