This paper revolves around women tourism entrepreneurs in the Pacific island nation of Samoa where an ancient way of living (fa’a Samoa) co-exists with colonial heritage and a growing tourism industry. By adopting a perspective sensitive to socio-cultural specificities, we examine the ways that the socio-cultural context both enables and impedes the empowerment of women managing tourism accommodations. In this venture, we draw on an ethnographic field study in the rural island of Savai’i, including semistructured interviews as well as informal conversations with locals, observations and the participation in everyday practices. We pinpoint and discuss the main sources of power and power-relations that women entrepreneurs need to command in order to run their businesses. Finally, we conclude that no (wo)man is an island, as we are all part of, and depend on, intrinsic social structures for our welfare.