Recent advances in semantic web and deep learning technologies enable new means for the computational analysis of vast amounts of information from the field of digital humanities. We discuss how some of the techniques can be used to identify historical and cultural symmetries between different characters, locations, events or venues, and how these can be harnessed to develop new strategies to promote intercultural and cross-border aspects that support the teaching and learning of history and heritage. The strategies have been put to the test in the context of the European project CrossCult, revealing enormous potential to encourage curiosity to discover new information and increase retention of learned information.