The importance of branding strategies, either in terms of brand architecture or the role of brand heritage, has often been put in the scope for the case of larger businesses. Yet, neither aspect has been explicitly investigated in terms of its role and contribution for smaller wine businesses. Focusing on the case of local family wineries in Crete, Greece, helps us identify links with and applications of both brand architecture and brand heritage literature. Findings suggest that most wineries do not use an umbrella brand to create relevant sub-brands but tend to build upon the house of brands or endorsed brands approach. Furthermore, wineries often refer to place brand heritage but family heritage is usually the cornerstone of their branding efforts. Our conclusions confirm the need to re-develop this body of literature in a way more adequate for small, family-owned wine businesses and enrich family wine businessmen’s understanding on the branding strategies.