This article analyses the structural challenges of the Latin American revolution in the early 1970s, which echoed from Fidel Castro's extensive road trip around Chile during the Salvador Allende administration in November 1971. Castro's presence promoted massive mobilizations of Chilean workers and peasants who came in droves to listen to his speeches. By then, an interesting dialogue between the Cuban and Chilean revolutionary paths had developed on a mass-collective basis, considering the dialogical skills of both leaders, Castro and Allende, who participated together in many mass demonstrations during the 24 days that the Cuban leader spent in Chile. While Cuba experienced an insurrection and guerrilla war, Chile was promoting a "peaceful road to socialism" through electoral victories. This article investigates the relations between the two revolutionary processes through the dialogues during this visit. This article is based on press materials from those days, Castro's and Allende's speeches and other primary sources. It concludes that the Cuban and Chilean Revolutions were more complementary than antagonistic, contrary to the historiography that emphasizes rivalry between them.