Determining the "wealthiest" Caribbean island depends on whether you measure by total GDP or GDP per capita, but as of early 2026, the Cayman Islands and Bermuda consistently top the list. Bermuda (often geographically grouped with the Caribbean) boasts a GDP per capita exceeding $110,000, largely driven by its status as a global hub for offshore insurance and reinsurance. The Cayman Islands follow closely, with a per capita income around $97,000, fueled by a world-class financial services sector and high-end luxury tourism. Among sovereign nations, the Bahamas is one of the wealthiest, with a GDP per capita of approximately $40,000, benefiting from its proximity to the United States and a robust banking industry. Other high-performers include the U.S. Virgin Islands and Aruba, which both rely heavily on sophisticated tourism infrastructure and refining. These islands stand in stark contrast to others in the region that face significant economic challenges, highlighting a massive wealth gap in the Caribbean that is often shielded from tourists by the glittering resorts of the more prosperous territories.