As a fortified medieval city, Dubrovnik was the centre of the Republic of Dubrovnik, one of the smallest states in the Mediterranean whose importance far surpassed its size. Just like in many other Croatian historic cities, its industrial heritage has remained in the shadow of the historic city, not properly acknowledged as an important segment of the city’s history. This dichotomy inspired this research, whose focus was the cradle of industrial development—Gruž Bay. The research focused on archival sources, published and unpublished materials and a field study. The systematic integration of collected materials was upgraded with an analytical study, the valorisation, contextualisation and, finally, contemporary presentation. Gruž Bay was once an idyllic landscape with few Renaissance summer villas. The original matrix was overlayed with pre-industrial and industrial complexes: shipyards, a harbour, a railway, industrial and infrastructural complexes. At the turn of the 19th century, they were slowly gaining momentum, which was suddenly interrupted by nearby political turmoil, and ultimately a war. Since then, tourism has prevailed, and the industrial complexes have gradually become redundant. The affirmation of the value of the industrial heritage and its potential for reuse would contribute to the further development of this well-known UNESCO site.