Ubiquitous information seeking systems have changed the way urban citizens understand and explore their world. At one time our five senses were the only way we could comprehend our surroundings, but now smartphones and other devices with access to social media have become bodily extensions which allow humans to expand their social interaction and sense what is “really happening”. This paper proposes research into serendipitous discoveries and casual mobile explorations enabled by context modelling over social media. This research will use the “surrounding context” concept as lens to present information and create aggregated views of what is happening with multiple visualization techniques like real-time ambient tag cloud and heat maps. The evaluation will follow a user-centred approached both in laboratory and naturalistic scenarios focussing on leisure.