The majority of the world's citizens now live in cities. Although urban planning can thus be thought of as a field with significant ramifications on the human condition, many practitioners feel that it has reached the crossroads in thought leadership between traditional practice and a new, more participatory and open approach. Conventional ways to engage people in participatory planning exercises are limited in reach and scope. At the same time, socio-cultural trends and technology innovation offer opportunities to re-think the status quo in urban planning. NeoGeography introduces tools and services that allow non-geographers to use advanced geographical information systems. Similarly, is there a potential for the emergence of a neo-planning paradigm in which urban planning is carried out through active civic engagement aided by Web 2.0 and new media technologies thus redefining the role of practicing planners? This paper traces a number of evolving links between urban planning, NeoGeography and information and communication technology. Two significant trends - participation and visualisation - with direct implications for urban planning are discussed. Combining advanced participation and visualisation features, the popular virtual reality environment Second Life is then introduced as a test bed to explore a planning workshop and an integrated software event framework to assist narrative generation. We discuss an approach to harness and analyse narratives using virtual reality logging to make transparent how users understand and interpret proposed urban designs.