Cruise ship passengers and all-inclusive hotel-guests are increasing exponentially as these floating and fixed properties proliferate in size and number. This is especially true for developing economies that consider sun, sand and sea tourism as a form of growth. Tightly integrated, multi-billion dollar global enterprises mix with weak local institutions populated by local officials, some corrupt, vying for more investment to create a toxic cocktail with diminished social benefits as the hangover. Within view of the shoreline and the towering monoliths of hotels and ships, post-secondary education facilities teach normative concepts of good management to students who, upon graduation, fight for a decreasing number of poorly paid jobs. Meanwhile, local government officials tout vacuous GDP figures and hospitality companies make inflated claims of employment to garner federal funding for infrastructure expansion. Many observers have made similar claims that have been easily ignored to date due to an absence of studies integrating tax revenue, private and public finance, and social outcomes. This combination illustrates not only current structures, but also how they are engendered. Rather than relying on tourist satisfaction, much investment is driven by windfall profits and tax-loss carryforwards thanks to tax loopholes and willing local officials that ignore or aid in the violation of regulations. While foreign companies condemn the corruption and cronyism at destinations, local nationals decry the exploitative foreign companies. The simple truth is that they flourish symbiotically. As such, this book necessarily addresses both actors. However, rather than being simply critical or numerical, this book provides recommendations for multinational enterprises increasingly running the risk of detection of aggressive tax planning and greenwashing. For host countries, it provides recommendations of a virtuous cycle for improved public sector accountability to restore the beneficial effects of tourism. There is also a discussion on how a value-added study of the tourism industry within a jurisdiction could detect untaxed profits that are withheld through astute transfer-pricing schemes. This is a book for tourism managers and experts, as well as policy-makers in the Caribbean and any sun, sand and sea destination that attracts floating and fixed all-inclusives.