This contribution reports the activities carried out by LamoLab, a non-governmental organization for multi-domain and multi-scale research applied to cultural terraced landscapes. Terracing and dry-stone walling have been internationally recognized as carriers of cultural values and traditional knowledge. Lamole in Chianti (Italy) has served as a primary case study of terraced vineyards, where interdisciplinary research has been converging for almost a decade. The evolution of multi-sensor data acquisition in different spectral ranges, data-driven modelling and multi-scalar approaches performed over the years are mentioned, with specific attention to the evaluation of microclimate variations induced by dry-stone walls and how they affect plant growth, ripening, and production. The results already obtained from data processing and analysis are described, although the work is still progressing. The ongoing research and future projects of LamoLab are reported for developing methodologies to understand the parameters that are critical for the effective restoration and functioning of the dry-stone walled vineyards and construct performance-oriented design strategies to enable knowledge-based design processes.