Reflecting on our efforts to provide Canadian university students with a transformative learning experience in Cuba, we were surprised to find that dominant forms of liberal thinking were more difficult to challenge than was anticipated. This paper explores this phenomenon and offers deliberation as a means toward lessening the stronghold of such beliefs. It begins with a sketch of our group participants and an explanation of our methodology, alongside the theory of cultural liberalism that frames the study. This is followed by a two-part description of our findings, suggesting that the liberal ideologies accompanying such innocuous practices as facilitating group harmony filter into understandings of democratic citizenship well beyond such parameters. We end with a tentative conclusion about the possibilities for democratic education in the increasingly complicated space of global interdependence and Cuban transformation in that space.