Cultural Heritage learners can highly benefit from ubiquitous learning approaches that connect in-classroom activities with active on-site learning opportunities. However, teachers face the problem that the current landscape of technological support for learning Cultural Heritage mostly consists of mobile applications for informal contexts, completely decoupled from curricular activities. This paper presents the results of an exploratory-sequential mixed-methods study that focuses on the feasibility, for non-technical expert teachers, of repurposing an existing mobile application in formal Cultural Heritage ubiquitous learning situations. Such feasibility is explored from the perspective of the orchestration metaphor. More specifically, we used the “5+3 aspects orchestration framework” to understand the orchestration challenges of four ubiquitous learning situations about Cultural Heritage carried out in two secondary schools. These situations involved five teachers and 139 students who used a mobile application called Casual Learn for several weeks. The results of the study suggest that, after a brief training, teachers can design, enact, and orchestrate ubiquitous learning situations that involve both in-classroom and out-classroom activities. The teachers were able to transfer to the students most of the orchestration load of out-classroom activities. The results also showed that the flow of learning artifacts and information between in- and out-classroom activities is a critical issue that needs to be addressed by developers of ubiquitous learning technological solutions.