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João R Freireis a professor at Ipam, Universidade Europeia in Lisbon, Portugal. His background in economics initially led him to work in the fields of finance and then marketing for several multinational companies in Brazil, Portugal and the United Kingdom. He is also the co-founder of two companies specialized in branding food and drink products. His greatest research interest is in branding and, more specifically, Place Branding. He worked in several projects in the area of Place Branding.ABSTRACT Branding is a complex concept to apply to a destination. One of the main challenges is the functional definition of the brand. Which area does the destination brand cover? It is relevant to acknowledge that political borders of a destination are not necessarily the same as the destination brand borders. The present article is a case study, which was a result of a consulting project requested by the Municipality of Cascais. Cascais is located in the Lisbon metropolitan area of Portugal. Described are the challenges faced by the Cascais Municipality in adapting its brand portfolio to a new context and different environment. Quantitative methodology was applied to understand the relevance of four destination brands for the tourism industry in the Cascais Municipality. A questionnaire was developed and applied in Spain and Britain, the two main tourist markets for the Cascais Municipality. From the research, it could be concluded that nationality influences the evaluation of destinations. It was also concluded that the environment where a brand exists is dynamic, not static. Therefore, the strategy developed for a brand has to be adaptable. This means that the brand role and mission might change over the years. Future investments and support for certain destination brands must be constantly questioned.Place Branding and Public Diplomacy (2016) 12, 78-90.