The aim of the present study was to identify sweet cherry varieties and growing regions that are resilient to climate change as well as strategies for mitigating the effects of climate change on sweet cherry production in a Northern European location (Meckenheim, Germany) and a Southern European location (Naoussa, Imathia, Greece). Sweet cherry was chosen for this study as it is sensitive to reduced chill accumulation (i.e., fewer chilling hours in winter) and to late frost damage caused by flower opening time advancement. Whereas initial predictions suggested that fruit growing in Southern Europe is particularly sensitive to climate change, our comparison of long-term records of both phenological (flowering) data and weather (frost, temperature) at both locations indicated the opposite. The annual mean temperature in Naoussa increased during 1984–2018 by 1.6 °C to 15.8 °C, whereas it increased during 1958–2018 by 1.5 °C to 9.8 °C in Meckenheim. In Naoussa, flowering was found to have advanced by 6.7 days in the late-flowering cherry cultivar ‘Tragana Edessis,’ but by as much as 8.3 days in the early flowering ‘B. Burlat,’ 1.5 days in ‘Vogue,’ and 3.2 days ‘Larian’ over the last 35 years (1984–2019). In the temperate climate of the Meckenheim cherry-growing area, flowering advanced by 14.1 days during the period 1978–2019 in the early flowering and early maturing cultivar ‘B. Burlat,’ such that it now coincides with the late spring frost. This flowering advancement in Meckenheim was almost twice that observed for ‘B. Burlat’ cherries in Naoussa. Thus, in contrast to what was previously thought, cherries grown in Naoussa may be more resilient to climate change due to the essentially frost-free climate during and after cherry flowering and the occurrence of sufficient chilling hours during winter. This strength may enable Imathia to export sweet cherries to Northern Europe in May, a time of the year when the fruit of this region is not yet available. By contrast, sweet cherry production in the colder climate at Meckenhein shows greater lowering advancement is more susceptible to frost (and therefore requires frost protection technology), making it less resilient to climate change.