Over the last decade, outbreaks of vaccine-preventable diseases have been reported in developed countries around the world. In particular, measles outbreaks have been ongoing in the European Union since 2017, with the majority of cases concentrated in Romania and Italy. Measles has been identified as a powerful indicator of the status of vaccination programs in a region, as outbreaks have been reported to quickly emerge as a result of underlying problems in the immunisation routine. This paper aims to report and critically comment on the factors underpinning the recent measles outbreaks in Italy, considering the psychological, cultural, social and political causes of vaccine hesitancy and refusal amongst the population. Data from government agencies including the Italian National Institute of Statistics (ISTAT) and the Italian National Institute of Health (ISS) are analysed to describe incidence and mortality trends from 1887 to the present day, including regional variations and the impact of measles vaccination coverage. The topic of compulsory vaccination is currently the object of heated debate in the Italian social and political panorama; this paper discusses the current state of the vaccination controversy in the Italian political discourse and its potential impact on immunisation policies and measles vaccine coverage amongst the population. A burgeoning body of evidence indicates that every effort should be made to bolster the existing legislation on mandatory vaccination through widespread health education campaigns aimed at improving scientific literacy amongst the Italian population with regards to the topic of immunisation.