Automatic methods for an early detection of plant diseases (i.e., visible symptoms at early stages of disease development) using remote sensing are critical for precision crop protection. Verticillium wilt (VW) of olive caused by Verticillium dahliae can be controlled only if detected at early stages of development. Linear discriminant analysis (LDA) and support vector machine (SVM) classification methods were applied to classify V. dahliae severity using remote sensing at large scale. High-resolution thermal and hyperspectral imagery were acquired with a manned platform which flew a 3000-ha commercial olive area. LDA reached an overall accuracy of 59.0% and a κ of 0.487 while SVM obtained a higher overall accuracy, 79.2% with a similar κ, 0.495. However, LDA better classified trees at initial and low severity levels, reaching accuracies of 71.4 and 75.0%, respectively, in comparison with the 14.3% and 40.6% obtained by SVM. Normalized canopy temperature, chlorophyll fluorescence, structural, xanthophyll, chlorophyll, carotenoid and disease indices were found to be the best indicators for early and advanced stage infection by VW. These results demonstrate that the methods developed in other studies at orchard scale are valid for flights in large areas comprising several olive orchards differing in soil and crop management characteristics.