This paper presents an investigation into the record breaking winter and summer maximum and minimum temperatures of 2007 across the Greek region. Three summer heat waves were analysed representing the highest maximum temperatures of the last six to seven decades. Winter minimum temperatures (mainly during January) were also found to be exceptionally high and they were proven to be more “statistically extreme” than the summer maxima. During the heat waves, an extended horizontal transfer of warm air masses from northern Africa was detected. The comparison of the results with future projections derived from a regional climate model revealed that these temperature conditions are likely to occur more than 50% of the time by the end of the 21st century.