This dissertation investigates Wang Meng’s landscape paintings of Daoist-inspired subjects in the context of Daoist culture in fourteenth-century Jiangnan China. By focusing on three of Wang Meng’s important yet less studied works, Cinnabar Mountain by the Ocean, Forest Chamber Grotto at Juqu, and Ge Zhichuan Moving His Residence, this dissertation illuminates the thematic diversity and stylistic originality in Wang Meng’s oeuvre and demonstrates how his broad range of empirical experiences and profound knowledge of Daoist sacred landscapes influenced his artistic practice. In the process, the dissertation also discloses Confucian-trained scholar-literati’s close association with Daoist priests and deep involvement in Daoist matters in the Yuan and illustrates one facet of Yuan literati culture’s religious and cultural diversity and inclusivity.The first chapter examines Wang Meng’s Cinnabar Mountain by the Ocean in the context of fourteenth-century literati’s exploration of Daoist sacred mountains and argues that the painting represents the topographical, historical, and religious geography of the coastal county, Xiangshan, in Zhejiang province, which was historically associated with the mythical island of immortals, Penglai. The second chapter analyzes Wang Meng’s Forest Chamber Grotto at Juqu within the visual tradition of grotto-heavens, a nexus of sacred caverns constituting Daoist sacred geography. The third chapter examines the thematic and stylistic origins of Ge Zhichuan Moving His Residence and explicates how Wang transformed the traditional subject matter of “moving residence” into a depiction of a sacred landscape. The last chapter expands the notion of a sacred landscape and explicates the idea of fengshui that underlies Wang Meng’s paintings of his friends’ and family’s residences. Overall, the dissertation demonstrates how the landscapes of terrestrial paradises created by Wang Meng catered to fourteenth-century recluses’ and refugee literati’s quest for a safe sanctuary during the tumultuous Yuan-Ming dynastic transition. At the same time, it pays particular attention to the artist’s own agency and contends that Wang Meng intended his paintings as venues for an “intellectual parade” to showcase his broad knowledge of art, literature, history, and religion.