Acknowledging and sustaining the ethnic and cultural diversity that the phenomenon of globalization has brought to the urban environment is one of the target objectives to seek spatial and social sustainability in today’s cities. This study aims to build upon previous research approaches that sought to characterize culturally diverse, urban public spaces. For this purpose, a method that encompasses digital and physical layers of information has been proposed to gather signs of culturally diverse, street-level urban and economic activities. Geolocated data from three social media platforms, as well as field-work observations, were collected from two case study street segments with different socio-cultural, demographic profiles. The findings suggest that economic activities related to retail and restaurants, and especially those with higher levels of personalization that reflect “cultural specialisms”, have a significative relevance in both the physical and virtual domains. However, unlike the case study area with the higher socio-economic profile, the urban vibrancy observed through field work throughout the more culturally diverse street segment was not found to be fully represented by social media data. There is still much room for research on the extent to which these sources are useful for characterizing fine-grain street-scale phenomena.