This article proposes to discuss a research/design methodology aimed at developing urban visions based on case study analysis of existing urban environments using Virtual Reality technology and Photogrammetry. In order to visualize possible scenarios for the city of the future the method described here is based on "drawing over" existing urban images whether in a 2D format or a 3D environment. As a preliminary to this creative urban design exercise the urban context of a specific street is analyzed both in terms of its physical and material qualities as well as its experiential ones. This methodology is tied to a pedagogical approach initiated at two different schools of architecture, one located in Nantes, France and the other in Tallahassee, Florida, US. The idea consists in having a team of students in each school engage in a case study of an existing street and then propose design improvements and scenarios for urban development and growth. The process would involve 3 steps; drawing over in 2D, drawing over on a projected 360° flatten image in immersion and finally sketching in 3D in immersion. This last step would allow a "co-presence" of students from both schools in a shared conceptual and design experience. Aside from the obvious differences between urban fabrics in Europe and the US, the value of this exercise would lie in comparing design approaches based on similar methodology but rooted in different geographic locations and urban design cultures. Faced with issues of high density, mobility, low economic growth, inequalities and sustainability, European cities have been under pressure to constantly innovate in terms of urban planning and design whereas the US has only seen such ideas of controlled density an urban environment quality gain traction in the past 20 years with such movements as the New Urbanism. The methodology described here is aimed at inspiring the creation of urban visions by means of using VR technology, photogrammetry and the idea of "drawing over". We see the value of this approach by combining the use of specific technologies and a positioning from two different cultural perspectives.