In 1430 Dubrovnik’s authorities decided to send ambassadors to the Sublime Porte for the first time. An important part of the preparatory activities was to decide to whom gifts should be presented, and what should be the nature and value of the gifts presented to the various recipients. Gifts were carefully wrapped diplomatic messages that their recipients could interpret in various ways. Gift rhetoric was used primarily to achieve strategic interests and was an ideological tool used both as a sign and an instrument. An analysis of the nature and value of the objects that ambassadors gave to their hosts reveals the “collective identity” of the community that preoccupied the City fathers, offers an insight into Dubrovnik’s trade connections and local production of luxury goods, as well as their reception in a different cultural landscape. Sources kept in the Dubrovnik State Archive allow us to reconstruct the list of Dubrovnik’s diplomatic gifts presented to various individuals at the Sublime Porte from the time of the establishment of the first official diplomatic contacts until the City became a tributary state. The gifts can be categorized according to the political and social rank of the recipients. Interpretation of the reasoning underlying the selection of gifts offers an interdisciplinary approach to the analysis of their pragmatic purposes, their origin and production, their value (economic, social, cultural, practical, emotional), and manipulation of their usage. As well as influencing both contemporary and future Ragusan - Ottoman relations, the gifts encouraged symbolic, material, and cultural exchanges between diverse civilizations.