The article intends to contribute to the literature on the relation between small cities and the creative economy in Europe. It aims to identify some dimensions and variables that need to be considered when approaching the capability of these small territories to attract creative people and businesses, surpassing the metropolitan-biased approaches oriented to the context of large cities. The research work is based on a case study methodology, centred on the comparative analysis of the small cities of Óbidos (Portugal), Barnsley UK) and Jyväskylä (Finland). The results of this investigation emphasise the context-specific nature of creative-based policies and stress the importance of some key success factors, such as governance and institutional arrangements, quality of life, entrepreneurship and networks