Within an EU Life project aiming to boost climate change adaptation in Greece, this study develops a transect method for rapid landscape-scale assessment. The procedure applies a holistic assessment of terrestrial landscapes at three spatial scales: a broad cross-section transect zone through the Peloponnese peninsula (240 km long, 1.416.6 km2) and successively the delineation of 35 selected landscape areas and the associated landscape views. Climate change scenarios and relevant indices were incorporated to screen for climate and anthropogenic impacts, including phytoclimatic, erosion and wildfire analyses. The climatic and bioclimatic conditions were examined in three time periods (reference period: 1970–2000 and in the future periods 2031–2060 and 2071–2100). Based on the above framework, the climate change adaptation planning process is reviewed including the Regional Adaptation Action Plan (RAAP) of the Peloponnese Region. The results of this method application effectively assess both the “territorial” and “perceptual” aspects of the selected landscapes; mapping the potential threats, interpreting problems, identifying knowledge gaps and prioritizing vulnerable areas. Analyses show that combined land-use pressures and climatic shifts will cause landscape change, particularly evident in an increase of wildfires, in the near future. Currently, poor conservation measures do not adequately protect landscapes in most areas of the study from expanding anthropogenic pressures (urban sprawl, wetland draining, etc.); these conditions may further aggravate environmental safety concerns during future climate change conditions. The review also documents poor attention to landscape conservation within the current RAAP report. The proposed transect method may assist in promoting landscape appreciation by setting an “enabling framework” for landscape-scale conservation planning during the climate change adaptation process.