The hospitality sector has great importance for the Cuban economy. Cuban hotels require more competitiveness to recover from the pandemic impact, adapt to the increasingly digital travelers and the global disruption of technology, in particular, the new digital business models in the tourism and hospitality sector. The inevitable digital transformation can help to increase the sector benefits. However, there are no documented procedures to identify the most impacting barriers in Cuban hotels in order to face this revolutionary change. This study aims to provide a reference to the identification of digital transformation barriers, considering it as one of the required organizational capabilities in order to properly manage such transformation. The work clarifies the importance of the barrier’s identification during the digital transformation process, provides a classification to group them in categories, and summarizes a collection of possible barriers according to literature review. In addition, the paper documents the procedure created to the barrier identification for the case study Hotel Nacional de Cuba and contributes with a practical and preliminary guide to systematize the procedure as a sustained capability.