The adaptive reuse of historic urban spaces for tourism brings both opportunities and challenges in interior design, requiring a careful balance between heritage conservation, contemporary functionality, and aesthetics. As cities seek to preserve their cultural identity while accommodating modern visitors, designers must address complex functional, material, spatial, and regulatory demands. The added value of this research lies in highlighting interior design’s role as a mediator between past and present, contributing to urban development and cultural continuity. The study investigates how contextual analysis shapes interior design strategies for transforming historic buildings into tourism-oriented spaces. Through a selective and comparative analysis of adaptive reuse projects in Romania, the research identifies best practices that maintain authenticity while catering to visitors’ needs. The methodological approach combines case study analysis, on-site observation, critical interpretation, and literature review, focusing on the ratio between the degree of architectural intervention in a given space and the cultural programming that caters to an attractive user experience. Key findings show that successful interventions are grounded in a deep understanding of the historical context and placemaking, as well as in a phenomenological grasp of what constitutes tourist attractions. Designers must preserve original architectural features while introducing new functions in ways that are respectful, reversible, and clearly distinguishable from the historical fabric. The main conclusion emphasizes that adaptive reuse, when guided by contextual insight and design sensitivity, enhances the cultural, educational, and economic value of historic sites. Thus, they become assets for tourism and hospitality developments and a context for events that attract the public. Interior design becomes not only a tool for aesthetic transformation but also a means of placemaking, stability, and historical storytelling. This approach fosters emotional connections between visitors and spaces, reinforcing local identity and increasing the uniqueness and attractiveness of repurposed urban heritage.