With the awareness that nowadays architecture faces new challenges, particularly the need of integrated and inclusive answers to the socio-cultural and environmental context, it is the objective of this re-search to develop the knowledge about undocumented exemplars of vernacular architecture in Portugal. Ver-nacular architecture is a significant information source about experimental evolution of ancient wisdom. The buildings studied in this research, by their isolation from network infrastructures are challenging examples for contemporary solutions aimed at self-sufficiency and sustainability. Recognizing the impact of the architec-tural design on lifestyles and in the environment and understanding the purposes that conducted to this type of building, this work aims at stimulating strategic thinking that connects architecture, landscape and man, seek-ing alternative and innovative solutions for a more sustainable architecture.