This research presents Dinko Ranjina (1536–1607), a member od the third generation of Ragusan poets, as a significant experimentator and innovator in 16th-century Ragusan poetry. His collection of poems Pjesni razlike (1563), which contains 441 od Ranjina's poems, is filled with innovations on the level of theme, meter, style, poetic idiom and conceptual level. It is pointed out that Ranjina's distinct reforming tendencies were shaped under the influence of contemporary Italian poetry, especially the poetry of court poets from the end of the fourteenth century, the so-called strambotista, whom he meets during his stay in Messina. It also points out other contemporary poetics that the author takes from Italian poetry, such as Neoplatonism and reformed Conchetism. It cautions against erroneous conclusions about Ranjina's knowledge of the Greek language, characteristic of older studies. Before the poems themselves, the prose dedication to Miho Menčetić is analyzed, the content of which is partly taken from the treatise of the Italian poet Bernardo Tasso Ragionamento della poesia, an important autopoetic manifestation in which Ranjina expresses his own views and opinions about literature, and is positioned according to the domestic literary tradition and its founder Šiško Menčetić and Džore Držić, and defends writing poetry in the vernacular. The analysis of the poems shows that Ranjina introduces new themes into love poetry, such as mythological and pastoral, new metrical forms, assimilates the sonnet form into domestic poetry, and introduces witticism as a dominant principle of poetic design following the example of the Italian Strambotists. His authorial self-awareness and understanding of literature as an evolving and changing practice are also highlighted. It is pointed out that although his reforming endeavors did not significantly affect the literature of his time, Ranjina was not a failed experimenter but an anticipator of the poetics of the coming 17th century and an important reformer of Ragusan poetry.