This paper examines Korean classical chinese poems on islands and islets with a main attention to their aesthetic features and literary significance. It discusses three spatial features of islands. First, islands represent a transitional space from this world to the other world; and from the real to the ideal. Such an image causes poets to make romantic purification of their sorrows and concerns in the secular society. Second, islands are communicative space between natural objects and self. Poets have imaginative conversation with objects, which is understood as communicative process to achieve harmonious unity with the nature. Lastly, islands plays a role of agent to turn poetic sentiments into transcendental imagination, which is difficult to observe in the case of the mainland. Two major poets of islands were Im Eok-ryeong(林億齡) and Yun Sun-do(尹善道). Living in Honam(湖南) region, they were actively involved in writing poetry despite conservative Neo-Confucian world view. Their poems are characterized as the expression of unrestrained spirit and romantic imagination which stood in contrast with the mainstream of Confucian rigorism at that time. They struggled with the somber reality filled with contradictions and absurdity but they did not yield to it. Instead, they confronted the real world and resisted social conventions. Therefore, their poems could achieve strong individuality and unrivalled sensitivity although their literary thoughts were based on stern Confucian principles.