Over the last few years we have witnessed the emergence of tools and languages that enhance our capacity to communicate the ways we communicate the idea of space, time and architecture. Recent developments in multimedia technologies and computer graphics, along with new communication models based on interactivity and the role assumed today by digital networks offer us completely new perspectives such as forms of 'experience' made possible by Hypermedia techniques, and to patterns of' presence' which are typical of VR technologies. Although the community of City Planners, Architects, Academia, City Officials and Policy Makers has finally started to ask itself how to integrate the new technologies into their practice we believe that still there is the need radically rethink the way we communicate design issues, local identity, heritage, and the models of communication with the public of such issues. This paper intends to present the experience carried out by our team over the last five years: the International Workshop 'Cities Design & the Internet', an opportunity for a group of scholars, professionals and students to gather, work and exchange experiences on design and city communication via the digital networks. The paper will discuss the case study for the proposed Val de Loire Unesco World Heritage Fund site Internet portal, whose prototype has been developed during the most recent edition of our workshop (July 2000) in Chinon, France. -- International Workshops City, Design & the Internet, organized by the Schools of Architecture of the Politecnico di Milano and the Universities of Ferrara and California at Berkeley: 1996, Copparo-Italy, 1997 Massa Marittima-Italy, 1998, Sassuolo-Italy, 2000 Chinon, France (in collaboration with UNESCO). Val de Loire web site: http://www.cdv.berkeley.edu/research/Val_de_Loire/index.htm