If the journey is politics, that is a human activity that involves going beyond one’s local, regional and national boundaries and relating to the Elsewhere and with the Other following legal or illegal procedures, then the journey of exile can be seen as the political journey par excellence, and as such can be observed through different lenses that help to understand its complexity. In this contribution, through some of the most complex and lasting cases of exile from Italy to Tunisia between 19th and 20th century, we intend to outline how diversified this life experience can be, how much it can be limited to being a brief parenthesis and how much it can sublimate to the point of becoming an inescapable paradigm of an entire existence. Within these two-time limits, the emphasis is placed on exile seen as an opportunity for training, for discussion and even for action in Elsewheres with respect to the favorite places of one’s political life rather than as an occasion for isolation, frustration and inaction, forced pause waiting for the return. In any case the exile arises as an existential condition in which the individual struggles to maintain his double presence, in his own land and in the host land, against his dramatic double absence. Therefore, rather than limiting himself to living in a forced Elsewhere, the exiled would seem to yearn to live between, at the physical and metaphorical borders of the Mediterranean space, in the hypothetical expectation of mending the wound of detachment, in a transnational and transcultural dimension.