The external entrepreneurial environment in any location comprises the different conditions that influence new ventures apart from those that are internal to the venture (Gartner 1985). Therefore, the new firm will be directly influenced by its location and its survival will depend on its adaptability and its ability to maximise entrepreneurial efforts within its specific environmental context (Aldrich and Martinez, 2001). The entrepreneurial environment “refers to a combination of factors that play a role in the development of entrepreneurship” (Fogel 2001: 103). In this paper, we analyse the assessment made by firms in small and remote islands economies, of the entrepreneurial environment in their region, by quantifying and evaluating key factors identified in the literature; and comparing and contrasting the findings with the assessment made by firms located in potentially more advantageous locations.