Tax havens have long been under the attention of numerous Governments and International Organizations which triggered the concern of an uneven playing field in the taxation area. As a result numerous amendments have been made to both their commercial and tax legislations in order to be in line with the internationally agreed tax standards. The aim of this article is to conduct a SWOT analysis on the offshore corporate structures found in the Caribbean landscape. Based on a selection process of the most commonly recognized tax havens in the Caribbean region and an analysis of their offshore companies at the level of incorporation, administration, activities conducted and costs, a set of frequently met characteristics have been identified which stand at the basis of the SWOT analysis. The results stand to present a comprehensive four dimension framework of the offshore corporate structures in regards to their strengths, weaknesses, opportunities and threats.