Until July 2021, the repercussions of the pandemic had been grave for tourism-dependent countries, such as Greece, and particularly the Cycladic Islands. The rest of the 2021 tourism season, however, proved especially successful for Cycladic tourism, which poses the question of why and how a tourism destination may survive—and even profit from—but also redevelop after the pandemic. Towards this goal, the paper engages in a critical overview and analysis of the relationship between culture and tourism in the Cycladic islands of Andros, Syros and Santorini, in the context of the anticipated regeneration of both cultural and tourism development, in the post-pandemic era.