Over the past few years, significant advancements are made in the acquisition, processing, analysis and interpretation of quantitative directional and high spectral resolution data. In particular, the broader availability of air- and spaceborne directional imaging spectrometer data supports the estimation of biophysical and -chemical variables with unprecedented accuracy and in calibrated physical units. We describe in this paper two experiments that we carried out to demonstrate regional performance of spectral and directional-based retrieval approaches in vegetated areas. In the first case study, we focus on a mountain forest located in South-Eastern Switzerland representing a boreal forest like ecosystem. DAIS7915 imaging spectrometer data have been acquired with simultaneous ground measurements. We describe the soil–vegetation–atmosphere radiative transfer using a combination of the PROSPECT, GeoSAIL, and ATCOR models. In the second case study, we acquired spectrodirectional data on ground using a field goniometer in parallel with several HyMap imaging spectrometer overflights. Both cases demonstrate conditions for the estimation of biophysical and -chemical canopy properties with reduced uncertainties by respecting the full spectral coverage and directionality of the data. We conclude that the derived canopy variables represent the actual spatial distribution of properties as they occur in the landscape.