The goal of this study was to investigate the differences in physical fitness in relation to urban or rural living environment and between two countries: Italy and Croatia. Over 14,000 students were tested during physical education (PE) lessons. Croatian students were taller and heavier than Italian students, with women achieving better results in flexibility. Urban students were fitter in abdominal strength than rural students. Age seemed to be the major factor influencing the performance. This study's results indicate a trend: urban students performed “indoor” tests better than rural students; the opposite may be true for rural students. Living environment, socio-economic-status, or cultural correlation differences could be decreased during school experiences. Thus, PE programs could train all people toward an adequate, age-based fitness level.