This paper presents a prototype for an educational toolkit (DIY GIS) to learn and teach some important elements of urban design, planning and management. The project aimed at developing a platform that addresses geographic mapping as a process that is subjective (of a projection of the user-inhabitant’s imagination) as well as objective (of the territory as a concrete structure). The platform applies text mining and conversation analysis to geolocalized user generated content (real-time data coming from Twitter, Facebook, FourSquareFoursquare, Flickr) in order to return meaningful visual images and maps about citizens' perception of public services, urban public spaces, and of the city as a whole. This platform has been developed and tested in some workshops with students in the field of architecture. From an educational point of view the platform itself can be considered a sort of toolkit that allows students to harvest, connect, analyze and interpret real-time data streams and to visually represent them in a personalized way. The students have to actively configure this toolkit in order to perform queries and design maps that are meaningful for the specific place under analysis and for their objectives. The paper focuses on both the design process of the toolkit and the first observations of the platform in use during some workshops carried out in the last months of 2011 in order to assess its education potential.