Using the title of the 54th International Psychoanalytical Association Congress as a motif, the author associates and develops metaphors that illustrate and relate how the historical elements of Portuguese culture may have a psychoanalytic understanding and how they impacted the Portuguese Psychoanalytic Society’s identity and work. Past and future, pride and sorrow, land and sea seem to shape the Portuguese psyche, creating a welcoming and conciliating nature forged from the tensions underlying troubled waters longing to be sailed.