In contrast to the highly modernised island-city state of Singapore today that has developed at a rapid pace, early Singapore was characterised by a starkly different living environment comprising a Malay fishing village before the period of European settlement. At the southern part of the island resided gypsies or boat people known as the Orang Laut, the indigenous peoples who lived along the coast, rivers, and other nearby and smaller islands. In the 1830s their homes were dotted along the Kallang River, the Singapore River and the bay area of Telok Blangah. The Orang Laut were probably one of the earliest residents of Telok Blangah, having been resettled under the British colonial government in the latter half of the nineteenth century. They made a living by ferrying people across the Singapore River, and by selling sweetmeats and fruits to crews of local vessels. Also known through other terms including ‘sea folk’, ‘sea roaming groups’, ‘maritime mobile groups’, and ‘sea hunters and gathers’, academic discussion pertaining to the Orang Laut shores up debates related to traditional notions of citizenship based upon bounded territories, borderlands, and state governance. Drawing upon preliminary archival research in Singapore, the chapter makes a case for how sensory experiences are built into discourses surrounding identity and livelihoods as sea nomads. How did the Orang Laut perceive and respond to flows of urban modernisation and development? How do they talk about resettlement or forced displacement? How do their sensory recollections of living with/by the waters reflect upon their sense of identity and communal life? What is the relation between sea and land within the wider discourse on Malays in Singapore? These are some guiding questions that the chapter attempts to engage with in order to consider how analyses contingent upon sensory studies and migration shed light on the Orang Laut community in Singapore and the wider region.