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This study analyses the migration of Gujaratis, ventures initiated by their business communities, their cultural engagements and continuities over generations in Singapore. The Gujaratis are a diverse group, linked through their ethno-linguistic roots, who constitute a minority within the Indian minority in the city-state. Their business acumen, cultural traits, food and festivities have contributed to the heritage and richness of the Indian diaspora in Singapore. A significant proportion of the Gujarati diaspora in Singapore, are descendants of immigrants who arrived during the colonial period and have a settled presence on the island for many generations. Over the last 30 years, a new layer has been added to the social fabric of the Gujarati community, as Singapore opened up to highly skilled professionals from the subcontinent, and as more Indian corporates and firms set up offices in the global city. The avenues and institutions established by the first and second generation of Gujaratis, the ‘old’ diaspora in Singapore, provided the foundation for these newcomers to adapt and partake in familiar socio-cultural events, religious practices and festivals in the new land.