This paper illustrates the Territorial Quality of Life (TQoL) measurement approach and its application in the cross-border area Trieste-Koper-Istria, a spin-off activity of the Espon QoL project in cooperation with the Slovene EU Presidency. Territorial quality of life is defined as the capability of living beings to survive and flourish in a place, thanks to the economic, social and ecological conditions that support life in that place. To measure the different dimensions of quality of life, a co-creative and deliberative approach is applied, engaging citizens, experts and policy makers in co-deciding what, why and how quality of life should be measured to promote a good life. The most crucial factor in this work was the citizens’ engagement, involving three main elements: living lab focus groups, digital contest and quality of life survey app. Selected key findings on the quality of life in the tri-national border region point to very wide disparities in quality of life between places.