Evidence from countries that achieved a high seasonal influenza vaccination (SIV) coverage suggests that reminders to get vaccinated may increase SIV uptake. The goal of this study was to explore the experience and attitudes of Italian adults toward an active invitation to receive SIV, triggered by different sources and delivered via different communication channels, and to assess the projected benefits of this strategy. A cross-sectional survey on a representative sample of Italian adults was conducted by using computer-assisted web interviewing. Responses from 2513 subjects were analyzed. A total of 52.2% of individuals previously received invitations to undergo SIV and compared with people who did not receive any reminder were three times more likely (68.2% vs. 22.2%) to be vaccinated in the last season. Compared with other sources, reminders sent by general practitioners (GPs) were perceived as the most attractive. As for communication channels, most participants preferred text/instant messaging (24.6%) or email (27.2%), suggesting an acceleration in the Italian digital transformation triggered by the COVID-19 pandemic. Conversely, traditional postal letters or phone calls were preferred by only 17.0% and 8.6% of respondents, respectively. Reminders sent by GPs via text/instant messages or email are a valuable option for increasing SIV uptake among Italian adults.