Education has been regarded throughout the years as one of the core societal values in Puerto Rico across different social classes. Parents make every effort to look for the most promising educational experience for their offspring. In this paper we present the findings of our ISSPP study conducted in two metropolitan Catholic successful prep schools, and a Math & Science specialized successful public high school. Data collection followed the standardized procedure for the ISSPP international study. Results show that these principals share the following set of characteristics: excellence attainment is a most important guiding principle; principal’s commitment is necessary in order to demand a serious commitment from students, faculty, school personnel and parents; they follow up on the most recent technological advances and are willing to risk and invest in high-tech educational technologies (i.e., e-books, smart boards, tablets instead of traditional notebooks, laboratory equipment, simulation software, computer lab); they are charismatic leaders who exert their influence in attracting students’ families to the schools, making them feel as part of the school success; they demand and hire highly qualified teachers (usually at the masters level); and they evidence a high degree of identification with the school and a sense of belonging.