This chapter adopts a strategic spatial planning approach to think strategically about potential joint place-branding initiatives between cross-border regions. The case study focuses on the extended cross-border European region composed of the NUTS III Alto Minho, Cávado, Ave, Área Metropolitana do Porto, Alto Tâmega, Tâmega e Sousa, Douro, and Terras de Trás-os-Montes of Northern Portugal and the provinces of A Coruña, Lugo, Ourense and Pontevedra of the autonomous community of Galicia in northwest Spain. Bearing in mind the mismatch of styles of regional government systems, the approval by the European Commission of the European Grouping of Territorial Cooperation Galicia–northern Portugal, and the current socio-economic environment, this chapter discusses the possibility of joining forces, procedures and strategic tools in order to enhance the reputation and give visibility to this European regional conurbation. In addition, this chapter intends to shed some light on the empirical significance of a cross-border place-branding strategy able to encourage entrepreneurship, job creation, trade and investment. It draws important lessons from the idea of interregional branding and aims to encourage a unique cross-border storyline. The chapter directly addresses the need to develop place branding, independently of the geographical scale of application, through a strategic spatial planning approach. Here the complex interregional branding exercises carried out by the Øresund and the Baltic Sea regions are taken as comparative cases. This chapter also aims to contribute to the academic debate on interregional place branding by discussing the potential development of place-branding initiatives across – administrative – border regions underpinned by knowledge from strategic spatial planning literature.