The concept of the smart city acquired increasing expression and has become a strongly discussed field in the recent past among, either the research community, either the political stakeholders. Studying and intervening on the urban dynamics requires a shift from focusing on forms of knowledge and innovation outputs towards focusing on learning and innovation dynamics, exploring the diverse dimensions of knowledge building and promoting social capital. This paper aims, first, to contribute to clarify the meaning of the word 'smart' in the context of urban development through an approach based on an in-depth literature review of pertinent studies and then, to establish the links with the dimensions of entrepreneurship that can help guide more effective urban development and planning policies, illustrating with the Smart Coimbra initiative. Besides the paper aims to inform and improve policy-making on the subject of promoting entrepreneurial mindsets and contexts, speculating on some principles and guidelines that may help fertilise urban dynamics and build smarter and more entrepreneurial cities. info:eu-repo/semantics/publishedVersion