The aim of the present research is to investigate the current situation of Romanian rural World Heritage Sites (WHSs) as potential smart tourism destinations. The trend toward developing smart destinations even within rural areas, though slower than in the case of cities and towns, is gathering momentum. Previous studies have shown the standing of identified Romanian WHSs within the broader settings of Romanian rural tourism development. However, since 2017 Romania’s WHS list was extended by one natural site, which includes multiple rural localities, and a new cultural site in a rural area nominated in 2021 (Rosia Montana, a rural locality). The research question for the present preliminary study was: are the Romanian rural WHS localities smart destinations? The paper adopts an exploratory multiple case study methodology where several bounded case studies are examined using multiple data collection methods. The originality of this paper consists of: (a) investigating the aspects of smart tourism in relation to rural WHSs in Romania; (b) the inclusion of all the current localities associated with WHSs, while most of the previous studies have the tendency to concentrate either on one rural destination or a geographical region. The answer to the research question is no. The investigated rural WHS destinations cannot ignore the unstoppable trend of smart tourism. Though late in introducing the digital technologies might prove a blessing in disguise since it allows the rural WHS destinations to learn from other destination’s experiences and to customize their future smart offer to their specific standings.