The author considers aesthetic thinking of George Santayana to be closely interconnected and knotted with his philosophical attitudes and at the same time with his art production (novel, poetry). The author suggests that his production (philosophical, aesthetic, literary, social, and political works), in spite of diversity of his ideas, can be characterized by continuity. She proves by evidence that Santayana’s thinking has not changed during his production despite the fact that he has used different approaches or terminology or style, medium. She points at the development of his thinking, shifts of opinions and ideas, which he has had on beauty, art, and life. She points out that his own ontological philosophical system has been developed gradually from his youthful aesthetic ideas. The author considers Santayana’s aesthetic thinking, especially his concept of “aesthetic experience” to be inspiring source for contemporary aesthetic and philosophical theories.