This paper focuses on the potential challenge for Italian democracy represented by the Five Star Movement (5SM). Its winning formula looks like a digital Utopia able to counteract the current political disenchantment: an influential blog connecting a horizontal network of citizens; a constant interaction between web tools and offline mobilization; the online selection of representatives. However, issues such as internal democracy and transparency, low levels of participation, and the ambiguous role of the leader (Beppe Grillo) have fostered criticisms and raised fundamental questions about its illiberal policy. The paper, confronting the party’s idealist approach to democracy with its contradictory political organization, contributes to the agenda of the panel in two ways: by presenting empirical evidence from an in-depth exploratory case study and by enlarging the theoretical debate about the role of web tools and their impact on the quality of democracy.