The career of the Jesuit missionary Giuseppe Castiglione, who was employed by the Imper ialHousehold in Beijing from 1715 to 1766, embraced two diverse artistic cultures: the European that framed the artist’s first training, and the Chinese that shaped his major professional achievements. This paper analyzes both Castiglione’s Italian training and painting knowledge, and some of his most exemplary Qing commissions in order to provide a framework for the cultural translation developed by the painter in China. Castiglione’s translation demonstrates that his foundational Italian training and the results he obtained later as imperial painter are profoundly interconnected. On this basis, the main aim of my paper is to discuss the system of dynamic, always shifting elements of connection of Castiglione’s oeuvre. These elements of connection are divided into three main contexts: the pictorial, the political, and the perceptual. They relate to three painting genres, which are crucial for understanding Castiglione’s enterprise: landscape, portraiture, and illusionistic perspective. On a broader level, the purpose of this paper is to show that the artistic career of Castiglione, when examined as an entire professional life, helps us to map out the points of cultural and artistic connectivity that facilitated encounters between China and Europe in the eighteenth century.