There is a strong interconnection between tourism and World Heritage Sites. This interconnection, on the one hand, can have a positive impact by presenting these sites to the public and helping generate conservation funds, but, on the other hand, if done unsustainably, can lead to their degradation. The adoption of digital technologies in tourism has made travel and visitations, even in remote areas, relatively easy. The adoption of new technologies at World Heritage Sites can also prove to be beneficial and help evolve a more sustainable tourism model at these venues. Furthermore, the new conditions due to the COVID-19 pandemic, while having a detrimental impact on global tourism, provide an opportunity to remotely promote and generate revenue to preserve a regions’ tangible and intangible heritage. A technology-based intervention, if adopted correctly, can help to develop sustainable visitation capacity and management at World Heritage Sites while also enhancing and enticing visitation at lesser-known sites. Case studies from Greece and India are presented to demonstrate how to increase visitation to lesser-known sites and enhance the overall tourism experience at these sites. A variety of digital tools are presented, from simplistic to technologically advanced ones. These digital tools could be adopted and used globally for other World Heritage Sites to enhance visibility and sustainability.