Security issues play a central role in influencing residents’ satisfaction towards everyday life in urban neighbourhoods (Gifford, 2007; Bonaiuto, 2004); moreover, safety is becoming the problem of our time, affecting individuals and communities (Amerio, 1999). Perception of safety in urban environment has been approached by many researchers in different areas of study, mostly sociological and criminological – and only recently by environmental psychology – in order to improve the quality of life in large cities. Safety and fear of crime are multidimensional constructs (Amerio, Roccato, 2005); they are influenced by a large series of either social or physical factors: signs of incivility, lack of control, social status, sociodemographic characteristics, social cohesion, sense of community, etc. The tradition of studies focused on perception of safety has been centered around numerous theoretical models and approaches such as indirect victimization (Skogan, Maxfield, 1981), community concern (Conklin, 1975), incivilities (Lewis, Salem, 1986), and subcultural diversities (Merry, 1981). Work from Taylor and Hale (1986), and from Covington and Taylor (1991) confirmed the importance of the central construct in each model and showed that no one model has more explanatory power than another. A more ecological approach (Bronfenbrenner, 1979; Becker, 1995) which takes into account a larger series of factors (also of different nature) could indeed help to clarify and to understand some of the dynamics existing between safety, fear of crime and the social/physical environment. Cumulative risk model (Evans, 2003; Evans, 2004; Evans & Marcynyszyn, 2004) – a model traditionally applied to developmental issues – is here proposed in order to clarify some of the dynamics existing between perception of safety, fear of crime and social/physical factors. A field study conducted in three different neighborhoods (safe, unsafe, and nor safe neither unsafe) of the city of Rome is presented. Results confirmed the cumulative negative effects of multiple risk factors on perception of insecurity/fear of crime and on well being/satisfaction with life. In particular, it is shown that as the number of risk factors rise, perception of insecurity and fear of crime increase, while well being and satisfaction with life decrease.