Contributing to the broader concept of a sociable smart city enabling a transforming society into a more participative domain where innovation takes place, the chapter addresses the economic revitalization of Middellandstraat, a multicultural shopping street in Rotterdam, The Netherlands. Through a growing influx of immigrants, Middellandstraat has evolved into a unique multicultural neighborhood with a similar mix of shops. This chapter aims to push the current envelope of the smart city debate by adding a culture-sensitive design perspective on placemaking. This elaborates upon learnings from a local contextually grounded design project in the context smart city revitalization challenge and promotes design as a means to improve and revitalize the street. After presenting the rich insights of the contextual study, the chapter describes the findings of the culture-sensitive design approach following its four stages and the resulting concept, called SmaakReis. Next, barriers and enablers of culture-sensitive design are discussed along five themes that are found key in designing for the revitalization of the shopping street and reflect on the value of design and cocreation. Based on the lessons learned, the chapter concludes with ten guidelines for smart urban design and implementation. It can be concluded that SmaakReis was helpful in codesigning futures with the local stakeholders and enabled them to act on the designed smart city vision in aligning their strategic activities. Interestingly the implementation of the SmaakReis concept in one of the local restaurants stresses the importance of capacity building and the relevance of the guidelines for cultural and local embedment