This study examines the intersection of digital transformation (DT) and business model innovation (BMI) within traditional “Made in Italy” sectors, such as Food & Wine, Fashion & Clothing, Home & Furnishings, and Automation. While these industries are renowned for their cultural heritage, they face the challenge of integrating digital technologies to remain competitive without losing their identity. The research explores how Italian firms in these sectors are navigating the balance between embracing digital innovation, particularly within the framework of Industry 5.0, and preserving traditional values. Industry 5.0, with its emphasis on human-centered innovation and sustainable practices, provides a lens through which to understand the evolving relationship between digital technologies and traditional craftsmanship. Through a qualitative multiple case study approach, this study aims to uncover how digital technologies, aligned with Industry 5.0 principles, are reshaping business models.