Is it possible for young people to develop intercultural understanding through an ocean-crossing sailing voyage? What would happen to intercultural communication in a tall-ship space? This article unpacks the process of interculturality construction and participants' identity negotiation within an ocean-sailing setting. It applies an analytical tool of intersubjectivity and seeks to relate interculturality to experiential learning theory. It draws upon a mini ethnographic study that collected data during a sailing voyage across the North Sea. The finding reveals six intersubjective factors that influence the process of interculturality co-construction. The article suggests that sail-training, as an outdoor medium of experiential learning, has the potential to stimulate participants to develop an analytical vision towards the self, the other and specific interactive dynamics.