The most problematic issues that characterize western society is the crisis of the subject and the difficulties of interpersonal relationships, leading to situations of deep distress and increasing the fragility of human beings. This behavior of the contemporary man also depends on flexibility rules in all areas of society and particularly inside the work, causing a significant impact on the character of individuals, reducing the expectations and hopes for the future, making flexible affective relationships. It is a fragile, insecure, unsatisfied self that waits all the year round for holiday and concentrates on it great expectations and hopes: the conquest of a new social identity, the self-realization, the development of communicative relations. Tourists prefer places with a strong link with nature, where it is possible to do open air activities, play sports and enjoy the beauties of the surrounding landscape. But in practical terms it must be said that holidays not always turn into such a perfect experience: individuals can barely satisfy their wishes and needs because of the difficulty in cutting themselves off from the routine life; moreover the pervasive machinery of tourist facilities tends to wrap in the consumer spiral even holidays’ places and times. Furthermore, the relation with the otherness reveals not to be exclusive only to the festive or vacation time, but it rather involves the whole existence of a person in his ethical and social dimension. The difficulties in fulfilling the wish for happiness through tourism depend perhaps on the impossibility of completely telling everyday life from spare time, which means that acting changes its modes, but not its substance.