Until July 2021, the repercussions of the COVID-19 pandemic were severe for tourism-dependent countries, such as Greece, and particularly the Cyclades. The cultural sector and related activities, at the crux of Cycladic tourism industry, were especially hit by the pandemic. The rest of the 2021 tourist season, however, proved especially successful for Cycladic tourism, which poses the question of why and how a destination may survive–and even profit–from the pandemic. This article thus explores emerging Cyclades tourism patterns and prospects (in a case study of Andros, Syros, and Santorini), in the context of the anticipated postpandemic tourism regeneration. Methodologically, the study was based on: a) a series of in situ in-depth interviews with key informants, b) a questionnaire survey of tourists and related local businesses, and c) a focus group panel discussion with key local/regional stakeholders. The study was conducted between the fall of 2020 and spring of 2021, in the context of the SPOT HORIZON2020 EU project; the research design and data interpretation were enriched by participant observation and consultation of Trip Advisor websites. Findings show that the pandemic and its repercussions were grave for these islands, highly dependent on tourism based on a dominant small-and-medium enterprise tourism development model. Modes of travel, types of tourism, and visitors??? behavior were altogether affected, resulting in new patterns of (im)mobilities, while the role of culture was viewed as the destination???s “hope in the horizon” towards the reigniting and regeneration of smaller scale, creative, dispersed, and more sustainable tourism. However, great disparities also emerged between the current state and regenerative potential for local cultural tourism development. The study participants specifically emphasized that the private tourism sector had been left by the State to their own devices, and pointed to a lack of a) cultural infrastructure, b) public funding, and c) destination marketing/promotion.