This paper discusses a virtual or borderless classroom exercise conducted by the National University of Singapore (NUS) and the University of Hawaii, Manoa (UHM). By reflecting on the experiences and views of the NUS participants, the article explores the possibility of virtual explorations as a substitute for conventional fieldtrips and fieldwork. The findings reveal that online interactions and experiences simulate some of the processes and outcomes of traditional field explorations. Online exercises also permit cross-country collaboration and trans-cultural dialogue between students in two campuses. On the other hand, virtual exchanges are limited by their static two-dimensional medium when contrasted with conventional fieldtrips, which provide multi-sensory experiences that better allow participants to understand a foreign environment, society and culture.