Background: Streptococcus pneumoniae is one of the leading causes of pneumoniae deaths, especially among elderly individuals, with the vaccine being the primary prevention instrument. However, information on national vaccine coverage among the elderly population is scarce and sparse. Methods: A survey involved a representative sample of Italians older than 65 years (n = 600), who agreed to participate in the study through a phone interview. Participants’ self-reported pneumococcal vaccination status, vaccine literacy, information source, and risk perception related to the infection and to vaccines-adverse reactions were assessed. Results: The reported vaccination status is very low (11.2%), with respondents largely uninformed about vaccination opportunities. The results also show that the predominant (and most effective) source of information is healthcare providers, with vaccine hesitancy being positively linked to risk perception related to disease and negatively linked to risk perception of vaccine adverse reactions. Conclusions: This study suggests the need to collect data to systematically monitor vaccination coverage and calls for information campaigns to improve elderly literacy to increase vaccination uptake.