A floating gallery, a drifting studio where sprawling waterscapes set off artwork on display and inspire original creation—the painting-and-calligraphy boat (shuhua chuan) may sound like a postmodern experimental installation. For its Ming patrons, however, it was nothing of the sort. Traceable to Mi Fu's floating gallery-cum-studio, the “art boat” was perceived as a beacon of cultural orthodoxy by generations of aesthetes like Mi Wanzhong, Dong Qichang, and Li Rihua. A nod to antiquity, it situated them in the continuum of long-standing tradition. The practice reached its acme in the mid- and late Ming, against currents of growing social mobility and dynamic imbalance that gave rise to a culture of connoisseurship as part of a fierce competition for social distinction. This paper examines the lure of waterborne art connoisseurship as cultural capital. Unique to the art boat is the act of collecting pieces for display and appraisal—an act akin to modern curatorial discernment. The selection of works that accompanied the patron onboard became an expressive medium. The painting-and-calligraphy boat also privileged a sense of fortuity. Chance encounters and spontaneous inspiration complemented the boats' movement along their free-form routes. Yet, the most prominent feature distinguishing the art boat was its visibility. Open panoramas of outstretched waterscape conjured a new creative avenue, a self-aestheticizing of both participant and vessel. This paper extricates the painting-and-calligraphy boat from its perception as a passing curiosity and shows it to be an enduring phenomenon that permeated premodern Jiangnan—the choice of the waterscape as a space of creation and recreation.