Art galleries brim with potential for rich experiences, but limited access to information and communication hurdles can often leave visitors disconnected. This paper explores how conversational technologies within art galleries can address visitor needs and enhance engagement. Previous studies have explored chatbots, AR applications in exhibitions, gamified quizzes, and indoor navigation algorithms, hence supporting the further research of this study. Through a habitat study, visitor–artist interactions were observed, followed by a task analysis focussing on the crucial conversation step. Investigating communication challenges in art galleries, this paper focuses on visitor difficulties such as initiating conversations, finding engaging information, and navigating awkward silences with artists. To address these issues, two types of solutions were proposed. The first was a headphone and tablet set with an AI-powered voice bot with feasibility as the main criteria. The second solution was smart glasses with the same AI-powered voice bot for innovation and convenience. UX writing further imbued the voice bot with a distinct personality, while low-fidelity and high-fidelity prototypes facilitated an interface for user interaction. The results of the conceptual testing elucidated the need for a product that provided an interactive and immersive experience in an art gallery. By demonstrating the potential of human–computer interaction to enhance visitor engagement, this paper not only proposes user-centred solutions but also lays the groundwork for future studies examining the solutions’ long-term impact, ethical considerations, and potential adaptation for other cultural institutions.