This theoretical-practical exercise responds to a real and emerging problem, arising from dialogue and a shared will to create a new reality. Although initiated between author and interlocutor — understood here as a client — the motivation goes beyond fulfilling a design request, aiming instead to address a broader collective need. The project focuses on the Alto Douro Wine Region, contributing to its built heritage and tackling urgent social issues linked to viticulture. The historical relationship between landscape and human labour raises questions about the evolution of seasonal workers’ ways of life. This essay reflects on that condition, considering the coexistence between local communities and recurring tourism. Quinta do Cruzeiro, in Vale de Mendiz, becomes the setting for testing a proposal that dignifies vineyard workers’ living conditions. The design is guided by principles of reversibility and adaptability, essential in temporary accommodation and in managing seasonal human flows. It is shaped by the region’s historical context, its man-made landscape, and by references to seasonal architectural strategies that inform key design decisions.