In recent times, there has been a worldwide trend towards creating smart cities with a focus on the knowledge economy and on information and communication technologies. These technologies have potential applications in managing the built and natural environments more efficiently, promoting economic development, and actively engaging the public, thus helping build more sustainable cities. Whilst the interest in smart cities has been widespread predominantly amongst metropolitan cities, several regional cities such as the Gold Coast in Australia have also recently endeavoured to become smart cities. In response to this emerging trend, this study aimed to investigate key opportunities and challenges associated with developing regional cities into smart cities using the Gold Coast as a case study. It identified key factors critical to the planning and development of smart cities. These factors fall under five broad themes: cultural and natural amenities, technology, knowledge and innovation precincts, people and skills, and governance. The factors were applied to the Gold Coast to analyse the key opportunities and challenges for its development into a smart city. Finally, key lessons, which are potentially applicable to other regional cities seeking to develop into smart cities, are drawn from the case study.