The article examines the problem of smoothing seasonal fluctuations in inbound tourism through the design and implementation of specialized off-season programs and itineraries. The relevance of the study derives from the fact that the temporal concentration of tourist flows intensifies the phenomenon of overtourism, undermining the economic resilience, social well-being, and ecological balance of destinations. This paper attempts a critical analysis of desezonalization strategies in the cases of Cyprus, Malta, and Georgia by extracting some universal factors that guarantee success. The novelty introduced here is by making a comparison between mature and developing destinations through their market structure, stakeholder coordination capacity prism, and an application of big-data analytics to air accessibility management. In methodology, it undertakes a systematic literature review. It processes official statistics on tourist arrivals for the years 2017 and 2023, in addition to comparing national strategic documents on product diversification, market development, transport infrastructure, and institutional governance. The main findings are: (1) without a paradigmatic shift from quantitative growth to higher revenue per tourist and quality of experience, formal diversification of supply does not work, (2) in mature destinations, political will and an embedded mechanism of inter-agency coordination decide, as evidenced by Malta that reduced the seasonality coefficient to 1.53, (3) developing markets can rapidly curb seasonality when they depend on data-based expansion of air networks and targeting market with reverse seasonality as demonstrated by Georgia, and finally (4) key barrier still lies within the implementation gap manifested through business model inertia and insufficient incentive for year-round operation. On this basis, a cyclical model of seasonality management is proposed, integrating long-term strategic planning, big-data analytics, and public–private partnership. The article will be helpful to researchers of sustainable tourism, designers of national and regional strategies, and destination marketing practitioners seeking to reduce seasonal dependence.