This paper presents a study of new technologies potentially enabling access to a sensory feast of places by ‘wired up’ flanêurs, real-time as well as remote ‘native’ description and interactions and situated oral histories excavated through ‘being in a place’. We describe an inter-disciplinary research project examining the cultural heritage of Singapore and the use of geo-location technologies incorporating social networking platforms as a medium for interactive heritage walks. The goal of the project is to engage both locals and non-locals in experiencing Singapore from a first person perspective, giving them a wider understanding of the ethnic and cultural diversity. The Living Avatar Network (LAN) supports sharing experiences and realities in real time through making it possible to ‘walk in someone’s shoes’ through a living avatar, re-experiencing someone’s memories of a certain place. Here we describe the approaches deployed in evolving a prototypical service - ‘traditional’ ethnographic style methods with the access to the real-time, lived character of ‘local’ experiences offered by digital photo streams and real-time video. More broadly, the project acknowledges the potential availability of the experience of being in a place and culture to be widely available through Web 2.0 technologies and people spending more time ‘living digitally’.