As cities with far-reaching diplomatic, mercantile and missionary networks, fourteenth- and early fifteenth-century Florence and Pisa were characterized by the impact of numerous artifacts imported from distant lands. This paper focuses on two case studies: The first one sheds new light on representations of Oriental carpets in the miraculous image of the Annunciation in the Florentine church SS. Annunziata as well as in its multiple ‘copies’, while the second one reflects on the impact of Mamluk metalwork from Syria and Egypt on late medieval and early Renaissance Italian panel painting. Contributing to recent art historical debates on transcultural dynamics, image-object-interrelations, and intersections between visual and material culture, this paper interrogates two site-specific cases of entanglements between the local and the global in the premodern period.