Our research seeks to analyse and discuss the variable ways in which the cultural and creative industries (CCIs) of the Cycladic Islands are viewed in their current state and in their regenerative potential for cultural tourism development, by key stakeholders in the Culture and Tourism sectors of the local society, economy and government. In particular, the paper engages in a critical overview and SWOT analysis of the selected stakeholders’ views, opinions and prospects regarding the relationship between culture and tourism in the islands of Andros, Syros and Santorini, in the context of the anticipated regeneration of both cultural and tourism development, in the post-pandemic era. The repercussions of COVID-19 pandemic have obviously been grave for tourism-dependent countries, such as Greece, and particularly the Cycladic Islands, likely to experience the negative impacts of the crisis more seriously than other economies and regions.