Outdoor Education (OE) is an educational approach that is spreading nationally and internationally in many countries, as a systematic analysis of the sector literature high-lights how it brings numerous benefits to the learning and development of literacy skills and transversal (Giunti et al., 2023). Thanks to its characteristics, including the flexibility of spaces and times, the OE offers the possibility of consciously using different technological devices, such as tablets and computers, before, during or after carrying out outdoor school activities, with the aim of planning and systematizing the work carried out and reflecting on the expe-rience achieved. Artificial Intelligence (AI) and Outdoor Education (OE) can adequately in-teract in profitable and interesting ways to enrich the educational experience at different levels and on different fronts, such as, for example, in terms of technologies for the knowledge of nature, analysis of environmental data, simulations and virtual reality, personalized learning, outdoor educational robotics and the promotion of environmental conservation, in an at-tempt to create more engaging and personalized educational experiences. This contribution focuses on the relationship between AI, OE and cultural heritage and how it can guarantee meaningful learning within school contexts.