Wine tourism (WT) is an important area of special-interest tourism in Portugal, and represents an increasingly significant component of regional development. In a more conservative approach, WT has been described as visiting vineyards, wineries, and engaging in wine-related activities. However, this perspective has been broadened, taking advantage of all the potential of the specific destination’s terroir (nature/landscape, tangible and intangible cultural heritage, etc.). Wine routes make the connection between wine and tourism in a specific region and intend to boost wine tourism by promoting collaboration between different stakeholders. Different routes present distinct approaches to WT, within diverse regional contexts, and different ways of collaboration within the wine route. This study compares three wine routes at different stages of development, located in a rural periphery – in the central region of Portugal – Bairrada, Dão, and Beira Interior, considering both context data and information collected in 113 interviews conducted with diverse wine tourism agents from these routes. Besides a brief characterization of the three routes, the main results indicate supplier’s preference for terroir routes instead of wine routes and show the importance of gender, age, and education level for the collaborative work between stakeholders. These aspects and their contribution to the development of WT routes are discussed. Some questions that additional studies may help answering are also reflected.