Among more dramatic effects, the COVID-19 scenario also raised the need for new online information and communication services, promoting the spread of software solutions whose usefulness will last well beyond the pandemic situation. Particularly in the cultural heritage domain, it has been unveiled the relevance of new AI-based approaches, able to dynamically aggregate information and making them available for a customized fruition aimed to the individual cultural growth. Here, we integrate machine learning techniques for the automatic generation of contents for an intelligent tutoring system grounded on automated planning techniques. We present a solution for semantic, intelligent creation of personalized cultural contents, born as a lesson-making assistant, but developed as to become a multi-function “cultural crossover”, useful in the frame of a wide range of planning, dissemination, and managing activities for cultural heritage contents.