Sustainable tourism development in the Caribbean is inhibited by several challenges such as diseconomies of scale and scope and other structural and resource constraints. These challenges are further exacerbated by the heavy prominence of transnational conglomerates who own and operate most of the large hotels, airlines, cruise ships, travel agencies and tour operators that market and control tourism on the islands. Foreign domination of the foregoing sectors has contributed to substantial leakage of foreign exchange revenues, social polarization, social exclusion and environmental degradation. While most Caribbean islands achieved constitutional independence from Europe, this did not necessarily involve a restructuring of economic relationships or a shattering of colonial ideologies. Today, the legacy of slavery and the plantation society underpins much of the regions’ contemporary culture, values and economic relationships despite the attainment of political independence. This paper aims to trace the nature and antecedents of foreign domination and control of Caribbean tourism and explores possible solutions to combat transnational intervention and economic dependency on them.