Tourism is an important employer for women in many countries. However, despite this seeming women friendliness, women are still underrepresented at the top of tourism businesses. Previous research on women managers careers in tourism has neglected the analysis of their careers in the light of new career concepts, such as the boundaryless career. Hence, in-depth semi-structured interviews were carried out with twenty-four female senior managers in Portuguese hotels and travel businesses, including entrepreneurs across a wide range of business sizes. The aim was to analyse these womens perspectives on how they have reached the top. It is concluded that women regard their careers as an outcome of their inherent characteristics, agency and a desire to seize challenges that lead to intrinsic satisfaction. They downplay the role of both structural enablers and structural barriers. This article analyses these issues from a boundaryless career model perspective and with a gender lens.