This paper focuses on the encounters between Italy and Siam at the dawn of the twentieth century, as it was the most dynamic period of Italian settlement in the modernising Siam. The paper analyses the development of Siamese modernisation as a challenging opportunity for Italian entrepreneurs and professionals, thanks to a healthy diplomatic relation between the two countries. Compared to the main characteristics of the Italian diaspora, the Italian colony in Siam stands out because of the fruits of its creative production. Siam was described as a symbol of tradition, not very different from the way China was often viewed, while the West was regarded as a source of modernity. With this perspective, the fact that Siam herself initiated the modernisation process, as well as the recruitment of Italians as part of the government's team in public works, architectural construction and civil engineering, was emphasised less than the part played by Italians in transforming the image of the Siamese capital. The paper examines how the encounters between Italy and Siam developed, attempting to do this from both Siamese and Italian perspectives, since both shared cultural memories, empirical evidence of cultural encounters and transculturality.