Planning of transportation infrastructure is built upon an established set of planning methods to estimate the need for and specifications of roads, amongst others. The abstraction from the real world as needed for applying clear planning tools has grown to considerably differ from the complex urban fabric of activities underlying the transport demand, such as food distribution, commercial activities, education networks, health, etc, especially in busy metropolitan areas. Inclusion of new parameters and use cases in design poses new methodological challenges. The socio-cultural context of urban areas provides for meaningful explanations for the use of urban infrastructure. The cultural context determines the expectations placed on the infrastructure by the people. For example, accessibility for the elderly and children, security and availability. Rapid urbanisation and increased economic inequality in cities has provided additional parameters to understand the longevity and contribution of transport infrastructure. The use of new methods such as the availability of real time data, sensor based data and additional social network analytical methods can provide new insights to understand the needs of the urban masses. Transport infrastructure needs to cater to local needs and become part of a larger ecosystem of a city. In this work we outline a new methodology to use games and simulations based upon city sensing to include stakeholders ignored by the traditional planning processes.