In multicultural contexts, health promotion can be challenging due to people’s differences in beliefs, values, and practices regarding health and healthcare. Using the prototypical case scenario offered by the “Health without Borders” program, this study was generally aimed at summarizing the lessons learned and suggesting implications that are hopefully relevant to future culturally competent health promotion programs. This exploratory study used in-depth interviews, focus groups, and document analyses as primary methodological tools to gather data. A qualitative approach was chosen because it has the potential to explore, in depth, the main characteristics (values, operational domains, and action strategies) behind this prototypical case. The study findings suggest that the multicultural health promotion program under study is characterized by four main intertwined core values (i.e., empowerment; peer education; social embeddedness; tailor-made). In turn, these values are expressed in the ten main operational domains (i.e., proactive approach to health promotion; fostering interculturality in health promotion; fostering multidisciplinarity in health promotion; measuring the impact of initiatives; identifying, training, and activating key community members in the role of peer educators; promoting community engagement; fostering a “domino effect”; building institutional links with the organization of the territory; continuous training of the professionals involved in the initiatives; flexibility and a constant focus on projects’ continuous redesign) that orient specific strategies of action. This program is based on a tailor-made principle for intervention design and delivery. This feature allows intervention providers to flexibly incorporate the target population’s values in delivering health promotion activities. Therefore, the value of this prototypical case lies in the design of “adjustable” initiatives that fit the “program-as-designed” with the cultural characteristics of target populations involved in the intervention.