Background: During the COVID-19 pandemic, more than ever, optimal influenza vaccination coverage among healthcare workers (HCWs) is crucial to avoid absenteeism and disruption of health services, as well as in-hospital influenza outbreaks. The aim of this study is to analyze the 2020 influenza vaccination campaign, comparing it with the previous year’s in a research and teaching hospital in Northern Italy. Methods: adopting an approach based on combined strategies, three interventions were deployed: a promotional and educational campaign, vaccination delivery through both ad hoc and on-site ambulatories, and a gaming strategy. Personal data and professional categories were collected and analyzed using univariate logistic regression. Vaccinated HCWs were asked to fill in a questionnaire to describe their reasons for vaccination adherence. Results: the vaccination coverage rate (VCR) was 43.1%, compared to 21.5% in 2019. The highest increase was registered among administrative staff (308.3%), while physicians represent the most vaccinated category (n = 600). Moreover, residents (prevalence ratio (PR): 1.12; 95% CI 1.04–1.20), as well as intensive care (PR: 1.44; 95% CI: 1.24–1.69) and newborn workers (PR: 1.41; 95% CI: 1.20–1.65) were, respectively, the categories most frequently vaccinated for the first time. Conclusion: the significant increase in vaccination coverage rate confirms the suitability of the combined strategy of delivering the flu vaccination campaign and represents a first step towards reaching WHO recommended vaccination rates.