The Haitian National History Park, which comprises the historical sites of the Citadel, Sans-Souci and Ramiers, is Haiti’s sole UNESCO World Heritage Site. The site aims to contribute to fostering a sense of community among all Haitians. Equally importantly, it seeks to instil a sense of national pride despite the negative image of Haiti conveyed by the popular media. All the attempts to turn the Park into a tourist destination have failed however, despite the site’s huge potential. On top of the political, economic and social issues faced by modern Haiti, the lack of leadership on developing tourism strategies also impacts negatively on the promotion of the site. This chapter considers the main difficulties of managing a Caribbean UNESCO site within a post-colonial, post-conflict and post-disaster context. Key issues that are faced include: lack of professionalism of tourism actors, lack of leadership and absence of vision, lack of knowledge of visitor needs and requirements, as well as the problematic external image of Haiti as a tourism destination. Although the focus of the paper is on a cultural heritage site, we raise wider issues here that have relevance to other debates around how heritage in an environment such as Haiti’s might be managed.