The paper engages in a critical assessment of the changes in cultural tourism largely due to the COVID-19 pandemic, from the period before to the period after the pandemic, as regards both the supply and the demand sides of tourism, through the eyes of local/regional/national stakeholders, in the case of the Cyclades, Greece. Methodologically, the study relies on a series of stakeholders’ interviews, a round-table discussion and a short questionnaire, undertaken in the context of the H2020 EU project SPOT, during the years 2020–2022. This material is then combined, using a SWOT analysis, in the context of a discussion and assessment of the problems, pitfalls and potential ensuing from the pandemic in Cyclades cultural tourism, towards a resilient, sustainable, or transformative future for the islands’ tourism and cultural sectors. The paper begins with an overview of relevant scientific literature, it continues with the presentation of the study’s research questions and data collection, and then proceeds to the analysis and discussion of the stakeholders’ opinions, perspectives, visions and recommendations on the changing relationship culture-tourism and the SWOT analysis. A general conclusion is that current and emerging trends and patterns seem to reinforce the reciprocal relationship culture-tourism, but also to reconfigure it, in line with new and evolving trends and patterns of cultural tourism.