Sound Travels constructs a biographical narrative of musician, musical director, showman and entrepreneur Ernest Kaleihoku Kaai (b. Honolulu 1881 – d. Florida 1962). It takes into account the extent of his musical practice and the scale of his touring in the Asia Pacific region at a time when colonialism was the defining cultural and political force. The narrative, while it looks at the context of his upbringing, broadly concerns a period between 1911 when he first visited Australasia to 1937 when he performed his final season in Singapore before returning briefly to Hawaiʻi and then settling in Florida. The relational and situational possibilities of cosmopolitanism will be used as a means for interpreting Kaai’s travels, engagements and intercultural encounters and his ability and apparent ease in traversing distinct social, cultural and political realms in a time period when imperial power dominated and racialised indigenous subjects. Cosmopolitanism also provides a framework for the discussion of the particularities of Kaai’s relationship to multiple discourses of identity, agency and representation and how those elements are reflected in his own syncretic cultural practice. Integral to this is a discussion of the “constant de-territorialisation of music-makers” (Slobin 1992: 6) and the role of music in facilitating spaces of transcultural exchange and mobility. Ernest Kaai and his Hawaiian Troubadours performed Kaai’s long running stage show A Night in Honolulu at the intersection of empire and entertainment in the early part of the twentieth century. Their travels through Australasia, India, the Dutch East Indies, Shanghai and Japan relied, for the most part, on imperial networks maintained by European and British powers. Kaai also participated in a nascent Pacific entertainment circuit1 that accompanied American imperialism in the Pacific where global cultural flows saw culture industries enabled, in tandem with technological, commercial and colonial developments, increasing access to emerging and existing markets for colonial entrepreneurs. This thesis locates Kaai at the forefront of performers who toured the South Pacific and Asia, opening the way for other Hawaiian musicians and popularising and localising Hawaiian music along the way. Kaai’s story constitutes a hidden history that has remained on the margins of popular music history because colonial historiographies have prevailed and overwritten non- European musical accounts. Kaai’s story and the collateral stories of musicians that travelled with him reveal understandings of Hawaiian music, the mobility of Hawaiian and other indigenous musicians in the early twentieth century, the cosmopolitan milieus in which they operated and the extent of their influence as musical stylists.