The aim of this paper is to offer an empirically grounded conceptualization of the dialogical relationship between spatial planning and place branding in the context of regionalization. The analysis displays the discursive nature of such relationship by highlighting the intertwining of spatial planning with place branding as strategic actions devoted to, and included in, regional development processes. The analysis is based on two cases in Sweden. The first is linked to the emergence of the brand ‘Stockholm, the Capital of Scandinavia’, and the other is linked to the emergence of the brand ‘Swedish Lapland’. By combining data collected longitudinally, these cases represent two contrasting examples of dialogical relationships that materialize through two distinct yet somehow similar strategic processes of regionalization. Based on the two cases, the paper presents and discusses an empirically driven, albeit conceptual, model that highlights the dialogical relationship of regionalization as regional strategic policy and points out its spatial and political evolutionary features.