In Italy, following the start of the SARS-CoV-2 vaccination campaign, community pharmacies (CPs) were recruited on a voluntary basis in order to administer COVID-19 vaccines as part of their activities. The aim of the present study was to investigate the knowledge, attitudes, and practices regarding SARS-CoV-2 infection prevention, and vaccine acceptance/hesitancy towards COVID-19 and influenza vaccinations among the community pharmacists operating in the Palermo Province. A cross-sectional study was conducted, with two different questionnaires administered before and after the conduction of the vaccination campaign against SARS-CoV-2 at the COVID-19 vaccination center of the Palermo University Hospital (PUH). The baseline survey showed that 64% of community pharmacists (CPs) declared that they planned to vaccinate against SARS-CoV-2, and 58% were vaccinated against influenza during the 2020/2021 season. Factors significantly associated with willingness to receive the COVID-19 vaccination were confidence in vaccines (adjOR 1.76; CI 1.11–2.80), fear of contracting SARS-CoV-2 infection (adjOR 1.50; CI 1.06–2.11), considering COVID-19 vaccination to be the best strategy to counteract SARS-CoV-2 (adjOR 1.79; CI 1.39–2.29), and adherence to influenza vaccination during the 2020/2021 season (adjOR 3.25; CI 2.23–4.25). The adherence among CPs of the Palermo Province to COVID-19 vaccination was 96.5%. From the post-vaccination survey, the main reasons for changing opinions on vaccination adherence were the introduction of mandatory vaccinations, fear of contracting COVID-19, and limitations on work activities in the case of vaccine refusal. The achievement of very high COVID-19 vaccination coverage rates among healthcare professionals (HCPs) in the present study was mainly due to the mandatory vaccination policies; nevertheless, a willingness for COVID-19 vaccination was relatively high among pharmacists before the beginning of the vaccination campaign. HCPs and CPs should receive training on vaccination, which is recommended in the national immunization plan and is also suggested by the respondents in our study, in order to routinely re-evaluate their own vaccination profiles, as well as those of their patients.