Starting off from images and movie song of Motorcycle Diaries, the Brazilian Walter Salles discusses the meaning of the practice of the then young medical student Ernesto Guevara de La Serna and Latin American perspective it raises. The Amazon River is central to these observations, as is the case with the novel The Raft (1881) by Jules Verne and The Stone Raft by José Saramago, published one hundred years later, in addition to Werner Herzog's film Fitscarraldo, the price of a dream. The river crossing is also featured as a theme in Guimarães Rosa's work and sets a discussion of the role of the intellectual, as well as the Atlantic crossings between the colonizer and the colonized. The crossings in theoretical and critical terms are problematized in terms of boundaries and identities. The prospects opened up by the short story "Orientation" (Tutaméia) by Guimarães Rosa, the novel by José Saramago and a symbolic crossing in the Angolan romance Pepetela (A generation of utopia), reverse the positivist outlook of modernity and evade being ossified by postmodernity. Such narratives spawn the discussion of historical, cultural and literary discourses of our times that naturalize the processes of networking and acceptance of asymmetrical cultural flows. In contrast to the habits of the managed society, leading to administration of difference in favor of established hegemonies, they develop the concept of concrete utopia, a youth principle, which is realized in the projects where supranational community horizons are key.