The article aims to survey the role of Greek entrepreneurs in the development of trade and shipping in the Black and Azov Sea area. Based on hitherto under-analyzed Ukrainian archival records of Greek communities (in Odessa, Izmail, Nikolaiev, Kherson, Feodosiia, Berdiansk, Mariupol, Taganrog, Rostov-upon-Don and Kerch), the article explores the professional activities of Greek merchants, captains, engineers, pilots and sailors during the nineteenth century and the early twentieth.