A number of researches investigating on tourism students' career choices and course of study selection have been widely documented. However, few studies have been carried out focusing on the process and context in which the Kenyan students make decisions about their careers. Therefore, this study provides an informed discussion of the relationship between tourism students' perceptions and their career choices at various levels of learning, using a comparative study of two public and leading training institutions in Kenya widely known to offer tourism courses. It was revealed that a large proportion of students at the diploma level would opt to pursue entrepreneurship for wealth generation and sustain their livelihoods as compared to the undergraduates who had more focus on further education and formal employment. The significant attitudes and perceptions of students studying at the diploma and undergraduate levels of study are deemed valuable to tourism trainers, employers, government officials, academicians, tourism professionals and tourism students on their path to continuously improve service delivery in the travel and tourism industry.