Cayman Islands

These three specks just south of Cuba and northwest of Jamaica make up a British Overseas Territory. Their inhabitants enjoy the highest standard of living in the Caribbean, thanks to the offshore banking industry. The crystal waters of Seven Mile Beach on Grand Cayman are the territory’s most famous attraction; the strip is also home to the main concentration of hotels. The islands are justly famous for scuba diving. Little Cayman’s Bloody Bay is consistently ranked as one of the world’s top wall dives, with a drop-off falling from 18 to 1,000 feet. And lying on the sea floor off Cayman Brac is the wreck of a Russian Koni-class frigate.

Note: In September 2017, Hurricane Irma hit the Leeward Islands with sustained winds of 180 mph, causing nearly $65 billion of damage. Many of our recommended resorts have now reopened. However, Eden Rock in St. Barths will remain closed until the end of 2019, as will Rosewood Little Dix Bay in the British Virgin Islands. And it seems as though Peter Island, also in the BVI, may never be rebuilt. Two weeks after Irma, Hurricane Maria arrived with sustained winds of 175 mph, causing $91 billion in damage. Fortunately, the affected Hideaway Report properties are now back up and running: Secret Bay in Dominica now has a new spa, and the St. Regis Bahia Beach Resort in Puerto Rico boasts a new restaurant pavilion and seaside bar.