This volume explores the multifaceted aspect of Utopia considered as an “extreme effort in imagination”. This approach implies a survey of the most powerful criticisms of the exiting as a possible alternative to approach urbanism. An effort able to conceptualize the city, the territory and the society against new backgrounds in order to understand the future. The reflection on Utopia investigates the need to find a stronger and more flexible language, adequate to describe the complexity of the different element of the contemporary. The urban project should reaffirm the role of a critical tool amongst actors and places, being a ground for representation and confrontation to finally contribute the exloration of reality. After today’s growing crisis and uncertainties in democracy, economy and society new challenges are established. They need to be understood through investigation and construction of innovative and original devices. Utopia, as for Bernerdo Secchi, is a specific mode developed by the Western culture to imagine the future, with the elaboration of the city and its design at its centre. Urbanism reflects on the best of possible worlds, not in an abstract way but, in Bernardo Secchi’s words, through the immersion of a wide number of practices and the conscius modification of the city and territory. Referring to the 500th anniversary of the pubblication of Utopia by Thomas More, this book is a collection of essays, scientifically peer reviewed by a network of scholars and academics in urbanism. They were originally presented in the first Bernardo Secchi’s study in November 2016 at the IUAV, University of Venice, sponsored by the Doctorate School of Architecturem, City and Design, the same school he taught for many years becoming a reference for several student generations.