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Trees are tall plants that can live a long time. They mutely attend events of humans for many years, even centuries, and millennia. A forest or a single tree can survive many human generations. When they get old, they can perform the social role as a monument, reminding the value of time and the environment. The present paper is dedicated to the Monumental and Legacy Trees in Sicily. It aims at showing the nexus between the necessary care of veteran trees and the cultural values that the entire society can achieve through their conservation for the present and the future. After the definition of Monumental Trees, the paper deals with the multiple meanings that even a singular tree has in religion, mystics, education, environment, heritage, and also in tourism. The paper gives geographical knowledge on the principal Sicilian Monumental Trees, deepening the fascinating stories of some of the more typical of them. The olive tree is a millennial symbol of the Mediterranean landscape; the almond tree remembers the eternal springtime of Sicily with its very early blossoming in February; oak trees, holm oak, cork oak, and chestnuts are gigantic monuments of the holiness and boldness of Sicilian mountains. The author argues that future life of old trees depends on policies regarding both environment and cultural tourism.