Giani Stuparich was one of the most important Triestine intellectuals in the first half of the 20th century. He was born in 1891 and died in 1961. He was a writer, a poet, a literary critic, an essayist. He also witnessed the tragic events that happened in Trieste and in Venezia Giulia during the First and the Second World War. He fought as a volunteer in the First World War. His brother, Carlo, and his close friend, Scipio Slataper, also volunteered as soldiers and died during the war. He was also a witness of the tragic events that happened during the Second World War. His works (novels, short stories, poetry, essays) give a lively description of Trieste, its most fascinating and suggestive places, the character of its citizens, and its charming story. This essay describes various journeys inside Trieste taken from Stuparich’s works. Some of these journeys are real, some others are metaphorical and metaphysical. The final result is an interesting description of an old and modern Trieste and its tragic events which took place during the two World Wars.