Heritage tourism of Bucovina region from Romania is passing through a decisive period for its’ survival, influenced by the rural-urban exodus, disappearance of traditional heritage, economic crises and even social crises. These factors influence a wide range of areas and stakeholders, from local communities, local entrepreneurs in tourism and their families, local administration and economy and cultural heritage preservation. A recovery of the tourism sector during these challenging period deals with safety procedures and confidence increase regarding the COVID-19 pandemic, capacity of digitalization and transparency of entrepreneurs, awareness campaigns regarding the beauty and importance of local heritage, stat aid schemes, national to local strategies. This study addresses the public (tourists, press, online influencers) perspective on Bucovina’s heritage tourism in the last period of time, using web scraping as a tool for extracting data from internet websites dealing with tourism. Based on these results, we are exploring solutions to develop policies, strategies and initiatives to sustain the entrepreneurial tourism in these troubled times. Our study can represent a starting point for understanding the impact factors of heritage tourism in Bucovina, the evolution of public perspective in the current economic and social context at large, the tourism digital economy and also on possible solutions for dealing with this evolution.