Developing an image of the city in an age of visual saturation appears to be a problem, precisely because awareness of the physical space of the city is disappearing or de-materializing-as a result of new digital information and communication technologies, as various theoreticians indicated. From the use of 3D city models and immersive virtual reality models of city to the use of telematics, telecommuting and advanced work environments that utilize Information and Communication Technologies (ICT), current urban and city planning theories and practices will inevitably change. Ultimately, we can learn valuable lessons from the urban structure of the “Internet” – the symbol of ICT. The impact and potential of ICT on the development of the urban environments in the 21st century carries along many promises of resolving some of today’s chronic problems of the urban environments.City and Urban planning in the Age of Information is, unfortunately, discussed in bits and pieces and thus the power of ICT is usually fragmented into scattered issues. Consequently, urban and city planners tend to misinterpret the overall picture. In some instances, this is a result of focusing on the most familiar issues that already gained momentum such as GIS. In other cases, as a result of the lack of a theoretical framework, the strategic and more conceptual issues are usually ignored. In doing so, a serious confusion between ICT tools and strategies take place, and thus blurring the line between ICT tools and strategies in urban and sustainable development.This paper attempts to discuss how urban planning strategies can creatively address the complex inter-linkages between ICT, urban forms and mobility in the City. It also attempts to encourage urban and city planners as well as architects to learn valuable lessons from the development of the “Web” – the symbol of Digital spaces.