During the height of the CoViD-19 pandemic in 2020 and early 2021, schools throughout Europe have been closed for several months, leaving teachers with the responsibility of providing distance learning through video conferencing and remote-presence systems, while parents were scrambling for appropriate tools and support. School outings have also suffered from the limited mobility of students given by stay-at-home orders and other restrictions. In this paper we present a set of technologies developed to reproduce the school trip experience, allowing students to stay at home or in school and requiring only a Web browser and Internet access, while integrating communication tools that allow participants to actively be engaged in interactive lessons and educational experiences. In 2020 the tool has been used during the “CodyTrip” event, a two-day visit to the town of Urbino, attended by more than 15.000 students, followed up with a series of events in 2021 with over 115.000 participants. Results from the pilot events show very high engagement and demonstrate the feasibility of organizing online visiting experiences with massive participation without compromising the perceived interactivity of the proposed activities, which can be equally engaging for different audience demographics. Findings also suggest that this solution may be adopted not only as a contingent substitute for traveling during the pandemic, but as an effective tool to widen the scope and appeal of cultural tourism.