In our understanding of tourism as a tool for development, small-scale enterprises are considered critical. From either the “trickle down” or “bottom up” perspective, small-scale entrepreneurs are considered central to the multiplier effect and economic development of communities in less economically developed countries. Whilst the potential exists for empowerment through entrepreneurship to be felt at an individual or community level, in many cases tourism does not lead to burgeoning entrepreneurial opportunities and the associated empowerment. This paper, based on long-term ethnographic research in Eastern Indonesia, examines the barriers to entrepreneurial development. It assesses why, in some communities, tourism offers the hopes and dreams of development and the initial steps towards empowerment, but why the dreams rarely become realities. Using Hofstede’s cultural dimensions as a starting point this paper identifies both cultural values and other factors that constrain, and support, entrepreneurship in tourism.