Reggio Calabria province (South Italy) is known for being almost the only area of cultivation of the bergamot fruit, grown principally for its essential oil, but today much studied for the health benefits of its juice. The biometrics and physico-chemical properties of the three (Citrus bergamia Risso) existing genotypes namely Castagnaro, Fantastico and Femminello were studied during fruit ripening from October to March. Castagnaro cultivar had the biggest and heaviest fruit during this harvest period. °Brix (7.9–10.0), pH (2.2–2.8) and formol number (1.47–2.37 mL NaOH 0.1 N/100 mL) were shown to be influenced by both the genotype and harvest date. Titratable acidity (34.98–59.50 g/L) and vitamin C (ascorbic acid) (341–867 g/L) decreased during fruit ripening. The evolution of flavonoids such as neoeriocitrin, naringin, neohesperidin, brutieridin and melitidin was studied both in bergamot juice and in the bergamot cloudy juice which is the aqueous extract of bergamot during fruit processing. Bergamot cloudy juice contained a higher quantity of flavonoids compared to the juice. This study gives important information regarding the cultivar and the harvest date for producers who want to obtain the highest juice quantity or the highest juice quality from the bergamot fruit.