By analysing three works of fiction set in Havana, Fresa y Chocolate by Tomas Gutiérrez Alea and Juan Carlos Tabi (Cuba/Mex./Spain/USA, 1993), Retour à Ithaque by Laurent Cantet (France/Belg., 2014) and Viva by Paddy Breathnach (Irl., 2015), we propose to study the Cuban capital as a sick body, as an architecturally, economically, politically and socially dilapidated organism. Its citizens struggle to survive, lacking basic necessities and trapped under a claustrophobic political and social surveillance, which the film directors convey through the use of a variety of aesthetic devices. There is a form of symbiosis between Havana and its inhabitants. The characters are confined in a labyrinth of alleys, stairs and narrow corridors, enveloped in a nocturnal atmosphere. The constricted arteries through which they move show that the body of Havana lacks oxygen. Its inhabitants need to find spaces to breathe and to express their authentic selves, to regenerate. This space is to be found behind Havana’s façades, behind its closed doors (an apartment, a cabaret) and even on a roof-top terrace. These private spaces reveal the dual nature of the city and its people, and constitute pockets of liberty as well as places of catharsis. The external façade presents a socially acceptable figure while covering and protecting the authentic self. The private spaces provide the physical and mental oxygen that the soul of Havana needs to survive. It is here that individual liberties flourish, allowing rights to be asserted, and art to be both preserved and created. The premise of a spiritual transformation begins to take form.