This chapter discusses two early initiatives aimed at creating urban environments especially suited for a car-free life one in the Austrian capital Vienna, and another in the southern German city of Freiburg. It explores the ways in which such initiatives aimed at shaping specific, local environments to potentially contribute to broader sustainability transitions. Together, these elements were meant to enable city dwellers to live an almost car-free life. The chapter builds on earlier research dealing with the Vauban model district and the car-free housing project in Vienna, examining these cases through the use of quantitative data and qualitative interviews with initiators and participants of the initiatives, as well as with document analyses of project-related materials and various additional studies. It provides historical descriptions as well as a brief comparison of the two cases as a basis for discussing the relevance of these locally confined initiatives for larger urban sustainability transitions.