Urban and periurban green spaces play an important role in preserving environmental resources and naturalness, with positive effects on people’s health and well-being. In this context, the study aims to model the relationship between the main ecological and psychological factors (e.g., biodiversity, perceptions, attitudes, evaluations, behaviors, etc.) that are related to urban and periurban green spaces. We focused on the psychological benefits and the general well-being associated with the use of green spaces. We selected five typologies of green spaces in the city of Bari (southern Italy), characterized by different physical features (e.g., presence of natural and built up elements, total extent of the area, distance from urban centre, etc.). A questionnaire focusing on people’s experience in the environment (length and frequency of visits, activities performed, perceived restorativeness, affective qualities of the place, perceived well being during and after the visits) was administered to users of five green space typologies. Results show that the perceived restorative properties are associated to typological characteristics of urban green spaces. Results suggest a mediating role of perceived restorativeness and length of the visits on the perceived well-being. We conclude by discussing the implications of the study on urban policies in the context of sustainability.