While much has been written about the history of mobility and trade in the Indian Ocean, recent trading connections between Eastern Africa and Asia have so far only gained very little attention. However, in Zanzibar alone, hundreds of traders regularly embark on journeys reviving old routes and further develop them, in order to take advantage of the way the global economy works today. By providing an ethnographic account of such a journey undertaken by four Zanzibari traders to Jakarta, this article gives an insight into the organization, calculations and imaginations involved in contemporary Indian Ocean trading networks. Although this trade journey clearly marks a new form of translocal mobility among Zanzibari traders, this mobile ethnography highlights how the journey is at the same time closely linked to, evokes and enlivens very old processes of mobility across the Indian Ocean, thus highlighting the dialectics between old and new mobilities, and between familiarity and strangeness.