Chronically ill conditions are particularly difficult to manage because of their impact both on the social and on the corporal sphere that negatively alter the quality of life. Chronicity has also a considerable effect on social capital. Chronic Venous Disease (CVD) includes several pathological alterations of the venous system of the lower limbs. The aim of this study is to explore the dynamics of social capital within people’s experience of CVD and describe the roles of family and friends and the health care system. The method used is based on face-to-face semistructured interviews, following the Consolidated Criteria for Reporting Qualitative Research (COREQ) checklist. Sixteen patients were included: eleven women and five men. The results show a certain difficulty in terms of daily activities, pain management; work problems; non-coverage of healthcare costs for medications and drugs prescribed. Moreover, the bonding social capital of the patients interviewed was more positively perceived in the role of CVD management than by the patients’ families. The total absence of knowledge of patient associations with CVD was also detected. Thus, alongside the biographical destruction that CVD entails, there is evidence of the scarce relevance and presence of health policies that cause several related issues.