The paper illustrates an experience in the teaching of urban design and planning carried out at the Politecnico of Milano where the School of Architecture offers a two-year Master of Science program in Urban Planning and Policy Design open to international students. In the first workshop, Urban Design and Planning Studio, the students are encouraged to challenge with experimental themes and innovative forms of urban design. In coherence with the recent experience developed at the Politecnico of Milano (Bologna and Milan, sharing the keyword “città di città”), the urban planning and design require a range of activities that generates knowledge, a survey conducted through design and imagination, through the ability to orient the information, systematise the data collected.