Augmented Reality (AR) is an alternative path of analysis and communication if applied to several fields of research, in particular if related to space and artifacts in it. This happens because the neural network development strengthens the relationship between augmented reality and artificial intelligence (AI), creating processes close to human thought in shorter times. In the last years, the AR/AI expansion and the future scenarios have raised a deep trans-disciplinary speculation. The disciplines of Representation (Drawing, Surveying, Visual Communication), as a convergence place of multidisciplinary theoretical and applicative studies related to architecture, city, environment, tangible and intangible Cultural Heritage, must contribute to the international debate. This Symposium deals with augmented reality and artificial intelligence, analyzing their connections as research tools for knowing the environment. In particular, its topics focus on the intersection between real and virtual world and on the heuristic role of Drawing in the enhancement and management of Cultural Heritage, in planning and monitoring the architecture, the environment, or the infrastructures. Scientists involved in AR and AI research applied separately or together in the field of Cultural Heritage, Architectural Design, Urban Planning, and Infrastructures Analysis are invited to contribute to the future international discussion focusing on the priorities and aims of the researches related to the disciplines of Representation.