Citrus fruits are extensively cultivated worldwide, with Italy and Spain being major producers. In Southern Italy, particularly in Reggio Calabria, a typical citrus fruit is produced, namely, bergamot (Citrus bergamia Risso et Poiteau), known for its mysterious origins and exceptional quality essential oil protected by the EU’s PDO (Protected Designation of Origin) designation. Despite historical challenges, bergamot has regained prominence for its nutraceutical potential, especially its flavonoid-rich juice, offering significant health benefits. However, little attention has been paid to understanding the qualitative and quantitative differences of bergamot juice in Calabrian production areas. For this reason, this work aims to investigate the quality characteristics of bergamot juice produced in different areas of Calabria sites. The results showed the best quality attributes of bergamot fruits harvested in the PDO area. In particular, higher levels of total soluble solids, stable acidity, and higher juice were found. In addition, higher contents of ascorbic and citric acids, which are nutritionally valuable and tasteful, were found. The phenolic profile, characterized by the key compounds of bergamot, highlighted the better nutraceutical potential of the fruit grown in the PDO area.