Urban design focuses on the structure and experience of the built and social environment, usually at the scale of a neighborhood or a district. Contemporary media tools allow us to envision environments at different scales, to propose designs with the current environment in mind, and to present that work to an audience varying in their political interests and design sophistication. New media tools have opened up opportunities for sensing, documenting, understanding, and representing the urban experience, for exploration and communication. What is striking is how tools go from being steep-learning-curve technologies, to readily-employed applications. So, I will focus here on general principles rather than on any particular technology or application. What is also apparent is that these media technologies and applications allow for new modes of understanding, while closing off others. Skills fundamental to the training of their teachers, are displaced by students’ new media methods. New forms of hand-eye/ear relationships, replace those of drawing, for example.