This article explores the conception, design, and implementation of a hypertextual map that we call hypermap. Using Giovanni Nolli's 1748 map of the city of Rome as a backbone, we conducted an experiment based on one of the routes defined by Giuseppe Vasi's Grand Tour of Rome to collect various types of urban and environmental information, thus aiming to connect a multiplicity of data from different nature and times periods to enhance the serendipitous elaboration of new narratives, interpretations, and data (namely "unfolding") not implicitly enacted by the pure analytical and mechanistic overlapping of gathered data ("folding"). This experiment is part of the research project entitled Datathink that was conducted at the Bibliotheca Hertziana - Max Planck Institute for Art History in Rome, the experiment serves as a proof of concept for an augmented database of the urban landscape in the city of Rome and new ways to facilitate the access and enhancement of cultural artifacts and knowledge.