The transition from natural Taiwan to cultural Taiwan plays an important role in positioning Taiwan's visual art during the colonial period. The reconstruction of the physical environment was a crucial step for the Japanese empire to implement in her colony of Taiwan. Physical nature therefore becomes a certain language containing psychological and emotional reactions towards such relationships. The paper intends to identify how some Taiwanese visual artists developed their landscape paintings, in comparison, how Yang Chih-Chang (楊熾昌, 1908-1994), a surrealist poet, conceived a different view of Taiwanese landscape poetry during roughly the same colonial period of the 1920s-1940s. Both sides paid attention to Taiwanese landscape and tropical scenery, but their terms of descriptive and reflective approaches differed. This interesting discrepancy shows that natural Taiwan has been endowed with cultural connotations and interpretations through the different media of visual and verbal representations and languages. Such perceptions also reflect certain value judgments and colonial relationships towards the Taiwan they inhabit. Between the objective and subjective, the literal and subverted, and the realistic and poetic, the Taiwanese landscape performed a different drama and meaning to their eyes. The way in which they conceived Taiwan therefore reveals how they discovered and represented colonial Taiwan.