Portals are the transition spaces between paths and places in an urban environment such as the entrance to a square from a connecting street. This paper aims to explore different forms of portals by considering their relationship with places. In doing so, a people-generated image analysis was adopted for two case studies conducted in popular Chinese recreational venues: Sanlitun Village, Beijing; and Xintiandi, Shanghai. Through an analysis of nearly 53,000Instagram photographs, three different roles that a portal can fulfil are identified and defined as the 'doorway', the 'showroom', and the 'place'. These typologies are derived from a deeper understanding of urban space through the 'eyes of the users', and this knowledge can in turn influence the design process for the public realm and urban spaces.