The growing focus on urban transitions has encouraged the development of innovative urban experimentations aimed at promoting active mobility and reclaiming the social function of public spaces, ultimately enhancing urban liveability. Among these solutions there are Street Experiments (SE). This paper aims to offer a holistic perspective on street experiments and on how they can improve the use and quality of public spaces. The methodology includes a comparative literature review to analyse the state of the art and identify factors influencing the location of SEs in urban contexts. Then, the paper presents a multiscale analysis encompassing urban, active mobility infrastructure, and neighbourhood-level assessments, based on Key Performance Indicators (KPIs). These KPIs support the development of a planning protocol for identifying optimal SE solutions. The results contribute to redefining SEs within contemporary planning scenarios, highlighting key barriers to their permanence. These include the contextual constraints, the regulatory framework, local administrations roles, and the evolving needs of urban populations.