Aware of the utmost importance of feeding premature babies—especially those of lower weight—with human milk, as well as the need to monitor this important element of neonatal care, we focused on four aspects in this review. First of all, we reviewed the beneficial effects of feeding premature infants with breast milk in the short and long term. Secondly, we performed a quantitative evaluation of the rates of breastfeeding and feeding with human milk in Very-Low-Birth-Weight infants (VLBWs) during hospitalization in the Neonatal Intensive Care Unit (NICU) and at discharge. Our aim was to take a snapshot of the current status of human milk-feeding care and track its trends over time. Then we analyzed, on the one hand, factors that have been proven to facilitate the use of maternal milk and, on the other hand, the risk factors of not feeding with breast milk. We also considered the spread of human milk banking so as to assess the availability of donated milk for the most vulnerable category of premature babies. Finally, we proposed a protocol designed as a tool for the systematic monitoring of actions that could be planned and implemented in NICUs in order to achieve the goal of feeding even more VLBWs with human milk.