In 1931, Ernest Hemingway wrote to John Dos Passos from Madrid: “You are the great writer of Spain”. The two friends both knew Spain, but Dos Passos got there first. In his early Spanish book, Rosinante to the Road Again (1922), Telemachus and his companion Lyaeus ramble along Spanish roads searching for “the gesture”, the essence of Spanish life that Dos Passos hoped to emulate in words. Spain remained important to Dos Passos, even after his famous break with Hemingway in 1937. The following year, Dos Passos exorcized Spanish ghosts in a second travel narrative, Journeys Between Wars (1938). Both texts present a multicultural and multiregional Spain, at odds with centralization and unification. In Rosinante, Spain serves as a testing ground for aesthetic experiments, as young Dos Passos searches for techniques that might articulate his resistance to American systems and narratives. The Spanish gesture communicates aesthetic and political choices, and the masculinity Dos Passos associates with opposition and pride. In Journeys, the author of U.S.A. concentrates on Spanish politics, but he relies on modernist aesthetics to intervene politically. Dos Passos satirizes both Nationalists and Republicans, who subscribe to measures and stories he could not decipher but hoped to deconstruct.Keywords: John Dos Passos, Ernest Hemingway, Modernist aesthetics, travel writing, Spain.