Monitoring the prevalence of breastfeeding is one of the actions provided for in Italian National Health System. This study aims to observe the prevalence of breastfeeding in a representative set of birthing hospitals in the province of Catania, in Sicily, Italy, to assess the factors influencing women in their decisions to breastfeed during hospitalization after delivery. We conducted an observational study on 3813 questionnaires administered to mothers of newborns during their hospital stay from the years 2016 to 2018 in eight hospitals of various types. The average maternal age was 31.3 years ± 5.8. Sixty-nine percent of women did not attend a prenatal course. From childbirth to discharge, the percentage of women who breastfed was 88%, of whom 45% did exclusive breastfeeding. Only 35% of women who had a caesarean section adopted exclusive breastfeeding. In our experience, rooming-in was not associated with an increase in breastfeeding. We observed that both attendance to prenatal courses and the mother’s education level played a minor role in influencing the mother’s decision in breastfeeding A fairly high percentage of exclusive breastfeeding, 75%, was attained just in one hospital, where dedicated staff was deployed to encourage breastfeeding. The lowest percentage (12%) of exclusive breastfeeding was observed in a large private accredited health facility. Hospital presence of professionals trained in human lactation is a smart investment for society.