This study explores the complex interplay of personal attitudes, community dynamics, and societal influences on breastfeeding experiences among women in Florence, Italy. Twenty-four women, aged 25 to 62, participated in comprehensive, 60-minute, in-person interviews conducted in May and June 2023. Four central themes emerged: 1) personal experiences, opinions, and attitudes, 2) communities involved in breastfeeding, 3) public opinion and culture, and 4) breastfeeding alternatives. Participants shared both emotional challenges and benefits, such as bonding and health advantages, while navigating the practical and social complexities of breastfeeding. Community support, including input from healthcare providers, midwives, and family networks, was crucial but varied in quality, sometimes offering encouragement and at other times presenting challenges. The findings highlight the individualized nature of breastfeeding durations, shaped by each mother's unique motivations and societal expectations. This study emphasizes the need for tailored support, public education, and comprehensive resources to foster positive breastfeeding experiences. The research advocates for policy and programmatic efforts that recognize and respect the diverse needs of mothers, promoting a supportive environment amid cultural and societal pressures.