Industrial hemp (Cannabis sativa L.) is a multipurpose crop with growing interest due to its environmental adaptability, low input requirements, and potential contribution to sustainable agricultural systems. This study evaluated the agronomic performance of four industrial hemp varieties grown under the edaphoclimatic conditions of the Alentejo region over two consecutive growing seasons (2024 and 2025) using different sowing dates. Phenological stages, plant height and growth parameters were monitored, complemented by meteorological data obtained from IPMA. The results revealed clear differences between years. The later sowing date in 2024 promoted greater vegetative growth, resulting in taller plants, while the earlier sowing in 2025 extended the vegetative phase and delayed flowering. Varietal differences were also observed, particularly for Fibror 79, which flowered slightly later, suggesting greater photoperiod sensitivity. These patterns confirm that both thermal environment and sowing date play a decisive role in hemp phenological development. The findings also highlight the high plasticity of the crop, which demonstrated strong adaptation to the hot and dry Mediterranean summers. Overall, appropriate selection of variety and sowing date can optimize vegetative and reproductive development, representing an important strategy for sustainable agricultural systems in the Alentejo region.