Every year we talk to travelers who are disappointed by a Caribbean trip. When we dig into why, it is almost always the same problem: they picked an island based on price or a social media photo, not based on what they actually wanted from the trip. The Caribbean is not one place. The islands are genuinely different from each other, culturally, geographically, in atmosphere, and in what kind of traveler they reward.
For first-timers and all-inclusive travelers: Jamaica or Turks and Caicos
Jamaica has the best personality in the Caribbean. Kingston has music, culture, and food that belong to it alone; the north coast between Ocho Rios and Port Antonio has some of the region's most dramatic scenery. Turks and Caicos, specifically Grace Bay Beach on Providenciales, has arguably the best sand in the Atlantic: powder-white, cool to the touch, and set in shallow turquoise water that looks retouched in every photograph but is not.
For couples and honeymooners: St. Lucia or St. Barths
St. Lucia has a landscape that does the work for you. The Pitons, two volcanic peaks rising from the sea, are among the most dramatic natural formations in the world. The island has a rain forest interior, black-sand beaches on the west coast, and boutique resort options that make it the most consistently romantic island we book. St. Barths is the luxury version: French in culture, impeccably maintained, with some of the finest small hotels in the Caribbean and a food and wine scene that would embarrass many European cities.
For sailors and island-hoppers: the British Virgin Islands
The BVI is the most sailing-friendly archipelago in the Caribbean. The islands are close together, the winds are reliable, the anchorages are sheltered, and the navigation is forgiving for intermediate sailors. The Baths on Virgin Gorda, a natural grotto of house-sized boulders at sea level, are the most photographed rocks in the region for good reason. Charter a catamaran out of Road Town and spend a week moving between Jost Van Dyke, Norman Island, and Anegada.
For culture and history: Cuba, Puerto Rico, or Martinique
Cuba has architecture, music, and a history unlike anything else in the Caribbean. Havana in the early morning, before the tourist traffic starts, is one of the great urban experiences in the Americas. Puerto Rico is US territory, which means US passport holders skip the customs process and spend the money they save on mofongo at La Casita Blanca in San Juan. Martinique is French Overseas territory: croissants, excellent wine lists, and Creole cuisine served with tablecloths at lunchtime.
For nature and diving: Bonaire, Dominica, or the Cayman Islands
Bonaire is a shore-diving paradise where the reef begins twenty meters from the beach and the marine protected area is pristine. Dominica is the most rugged island in the Lesser Antilles: volcanic, forested, with boiling lake hikes and sperm whale watching that rivals the Azores. The Cayman Islands have the most accessible reef in the Caribbean for recreational divers, and Stingray City, a sandbar where wild southern stingrays have been visiting since fishermen started cleaning their catch there in the 1980s, is the most memorable snorkeling experience in the region.
When to go, and what hurricane season actually means
High season runs December through April: dry, comfortable, and more expensive. The off season of May through November includes the official hurricane season, but this does not mean it rains constantly. It means there is a possibility of severe weather, particularly August through October. Many travelers visit in May, June, and early July with no issues and hotel rates 30 to 40 percent lower than peak season. If you go during hurricane season, buy travel insurance with trip interruption coverage.
