This paper discusses the learning and educational potentialities of the Venice Unfolding prototype, an experimental tabletop application designed to explore and investigate urban and territorial contents and knowledge. The prototype supports and transforms ways of approaching various strategies involved in urban and territorial planning processes. It creates new ways of viewing, understanding and learning about urban and territorial environments and leads to a more efficient examination of their underlying characteristics. In doing so, it fosters greater knowledge generation about their use, evolution and growth. In this paper, the authors describe the prototype’s development, its fundamental concepts and its considerable instructional capabilities that have been piloted with educators and students.