Caribbean firms cope with international competition both in their small domestic economies and as they extend their operations outside their home countries. This volume explores their struggles and successes in fifteen case studies developed from interviews with Caribbean firms at key decision points in their internationalizing processes. The cases ask the reader to offer direction; to evaluate choices made or to opine on paths not taken. The cases feature over thirty countries in the Americas, Europe and the Caribbean. These appear as markets, domiciles or hosts of subsidiaries of the internationalizing Caribbean firm. For example, one of the Barbadian cases describes a food caterer operating in ten countries in South, Central and North America. The cases cover multiple industries including cement manufacturing, supermarkets, shipping, remittances, banking, tourism, rum production, shrimp harvesting, food manufacturing and airline catering, and reflect the conversations with practising managers, who raised such questions as, “How does one define the Caribbean manager?” “How do we exploit our diaspora markets?” “How can small firms scale up?” “Where should we locate headquarters?” “What should be the role of regional governments?” “How do we pick allies and manage alliances?” The managerial challenges described are diverse: decision-makers from GraceKennedy, Goddard’s Enterprises or Trinidad Cement Group share practical experiences including decisions on marketing (e.g., pricing and retail locations); financing and accounting (e.g., alternative financing options); international strategy (e.g., alliances and take-overs); corporate governance; operations and personnel. All fifteen cases add to understanding emerging market multinationals, particularly those domiciled in small island developing states characterized by tiny internal markets, limited international influence and environmental fragility. They add insight to work on Caribbean entrepreneurship, business and economics and to studies of international business in developing countries.