In response to the epidemic of non-communicable diseases (NCDs) in the Caribbean, the Heads of Government of the Caribbean Community (CARICOM) issued the 2007 Port-of-Spain Declaration, “Uniting to Stop the Epidemic of Chronic Non-communicable Diseases” and declared the second Saturday in September to be “Caribbean Wellness Day” (CWD). CWD is a call-to-action for engaging the population of the Member States in confronting NCDs and their risk factors. This report reviews the genesis, implementation, and institutionalization of CWD in CARICOM and beyond. The study used quantitative and qualitative methods, including 29 surveys, 7 in-depth interviews, and analysis of media content. Data was provided by NCD focal points at the Ministry of Health in 15 CARICOM countries, as well as by 7 nongovernmental and 4 private organizations. Branding materials were well received and locally adapted; much of CWD media content originated from organization websites and were not community-based. Events typically focused on physical activity and health screenings and were attended by up to 3 000 participants. Though most were held in city centers, some CWD activities have involved rural and indigenous populations. CWD has become a catalyst for multisectoral engagement and health promotion activities. Inspired by CWD, PAHO initiated “Wellness Week in the Americas,” which includes CWD and promotes its tenets across the Region of the Americas. As CWD further develops, consideration should be given to reliable, adequate, and sustainable financing; to measuring and evaluating its impact on NCDs; and to widening its reach to include those outside of city centers.