Contemporary crop research programs involve the evaluation of numerous micro-plots spread across extensive experimental fields. As a result, there is a growing need to depart from labor-intensive manual measurements when assessing phenological data. The growing significance of high throughput phenotyping platforms (HTTP), including unmanned aerial vehicles (UAVs), has rendered these technologies essential in crop research. The overall objective of this study is to explore and validate the use of HTTP methodologies, specifically the potential of vegetation indices (VIs) derived from conventional RGB images, to forecast the date of heading (DH) and maturity (DM) for various cereal crops under different irrigation conditions. To pinpoint DH and DM prediction, a total of nine UAV surveys were conducted throughout the entire crop cycle. Prediction models for DH and DM using VIs were successfully developed for various crop species, explaining 65 % of the variance in bread wheat and 75 % in oats. The highest percentages of variance explained were achieved when models were developed separately for the two irrigation conditions (well-irrigated and rainfed). However, the percentage of variance explained by these models decreased when applied to barley (R²<0.5 for DH). Notably, including final plant height as a predictor increased the percentage of variance explained by the models only for irrigated bread wheat. Furthermore, the utilization of multi-temporal equations, which amalgamated data from diverse UAV surveys, notably enhanced the percentage of variance explained by the model (+160.71 % improvement in DH predictions), particularly those tailored to each specific crop species and irrigation condition. The investigation additionally established a thorough protocol for modeling the phenological aspects of cereal crops utilizing data acquired from UAVs, thereby enhancing the accessibility of this technology for measurements of phenology in large crop research programs.