Climate change and water scarcity are major threats to the sustainability of wheat production in Mediterranean regions. Thus, timely and reliable water demand assessments are crucial to drive decisions on crop management strategies that are useful for agricultural adaptation to climate change challenges. Although the AquaCrop model is widely used to infer crop yields, it requires continuous field-based observations (mainly soil water content and crop coverage). Often, these areas suffer from a scarcity of in situ data, suggesting the need for remote sensing and model-based decision support. In this framework, this research intends to compare the performance of the AquaCrop model using four different input combinations, with one employing ERA5-Land and crop cover retrieved by satellite images exclusively. A field experiment was conducted on durum wheat (highly sensitive to water stress and playing a strategic role in national food security) in northwest Tunisia during the growing season of 2024–2025, where meteorological variables, green Canopy Cover (gCC), Soil Water Content (SWC), and final yields (biological and grain) were monitored. The AquaCrop model was applied. Four model input combinations were evaluated. In situ meteorological data or ERA5-Land (E5L) reanalysis were combined with either measured-gCC (measured-gCC) or Sentinel-2 NDVI-derived gCC (NDVI-gCC). The results showed that E5L reproduced temperature with RMSE < 2.4 °C (NSE > 0.72) and ETo with RMSE equal to 0.57 mm d⁻¹ (NSE = 0.79), while precipitation presented larger discrepancies (RMSE = 4.14 mm d⁻¹, NSE = 0.58). Sentinel-2 effectively captured gCC dynamics (RMSE = 15.65%, NSE = 0.73) and improved AquaCrop perfomance (RMSE = 5.29%, NSE = 0.93). Across all combinations, AquaCrop reproduced yields within acceptable deviations. The simulated biological yield ranged from 9.7 to 11.0 t ha⁻¹ compared to the observed 10.3 t ha⁻¹, while grain yield ranged from 3.0 to 3.5 t ha⁻¹ against the observed 3.3 t ha⁻¹. As expected, the best agreement with measured yield data was obtained using in situ meteorological data and measured-gCC, even if the use of in situ meteorological data coupled with NDVI-gCC, or E5L-based meteorological data coupled with NDVI-gCC, produced realistic estimates. These results highlight that the application of AquaCrop employing E5L and Sentinel-2 inputs is a feasible alternative for crop monitoring in data-scarce environments.