We introduce a field survey method to assess the conservation condition of landscapes. Using a popular rapid assessment format, this study defines observable “stressed states” identified through the use of general metrics to gauge landscape degradation. Fifteen metrics within six thematic categories were selected through a literature review and extensive field trials. Field tests on the Greek island of Samothraki show a strong correlation between a single expert’s scores and five assessor’s scores at 35 landscape sites. Only three of the metrics did not maintain a high consistency among assessors; however, this is explained by the difficulty of interpreting certain anthropogenic stressors (such as livestock grazing) in Mediterranean semi-natural landscapes with culturally-modified vegetation patterns. The protocol and proposed index, with five conservation condition classes, identified areas of excellent and good quality, and reliably distinguished the most degraded landscape conditions on the island. Uncertainties and difficulties of the index are investigated, and further research and validation are proposed. The protocol effectively goes beyond a traditional visual aesthetic assessment; it can be used both by experts and non-scientists as a conservation-relevant multi-disciplinary procedure to support a holistic landscape diagnosis. The combination of an on-site experiential survey and its simple integrative format may be useful as a screening-level index, and for promoting local participation, landscape literacy and educational initiatives.