Montego Bay has two distinct faces: there’s the smooth tourist countenance that grins contentedly from the pages of a thousand glossy Caribbean brochures; and there’s MoBay proper, a pretty gritty city, second only to Kingston in terms of status and chaos. Most of the big all-inclusive resorts are located well outside the urban core in the fancy suburb of Ironshore.
Squeezed between the Blue Mountains and the world’s seventh-largest natural harbor, Kingston simultaneously impresses you with its setting and overwhelms you with its noise and hustle. This is the island’s cultural and economic heart, and a place named a Creative City of Music by Unesco in 2015.
Trinidad & Tobago
Trinidad and Tobago are an exercise in beautiful contradiction. In Trinidad, pristine mangrove swamps and rainforested hills sit side by side with smoke-belching oil refineries and ugly industrial estates. Tobago has everything you’d expect from a Caribbean island, with palm trees and white sand aplenty, yet it’s relatively unchanged by the tourist industry.
US Virgin Islands
Hmm, which of the US Virgin Islands (USVI) to choose for hammock-strewn beaches, conch fritters and preposterously blue water? Easy: any one, though each differs in personality. St Thomas has more resorts and water sports than you can shake a beach towel at. It's the most developed island, with dizzying cruise-ship traffic.
Santo Domingo, or ‘La Capital’ as it’s typically called, is a collage of cultures and neighborhoods. It’s where the sounds of life – domino pieces slapped on tables, backfiring mufflers and horns from chaotic traffic, merengue and bachata blasting from corner stores – are most intense.
South Coast & Central Highlands
Cut off from the clamorous north coast by the natural bulwark of Cockpit Country and protected from resort development by local communities that seriously value their near-virgin beaches, southwest Jamaica feels like a clandestine paradise for the trickle of off-island visitors who make it this far.
Blessed by nature, St Lucia has geographic and cultural riches enough to embarrass far bigger nations. Notwithstanding, it remains a down-to-earth place that wears its breathtaking beauty with nonchalance. Noted for its oodles of small and luxurious resorts that drip color and flair, it is really two islands in one.
St-Martin & Sint Maarten
The world's smallest area of land divided into two nations, this half-French, half-Dutch island's fascinating cultural mix incorporates a rich African heritage and 120 different nationalities speaking 80-plus languages, giving rise to some of the finest cuisine in the Caribbean. A major cruise-ship port and air hub, St-Martin/Sint Maarten's number-one focus is tourism.
While it's justifiably famed for its fantastic beaches, Barbados is an island that has it all. In addition to fine powdery sand and brilliant turquoise bays, you'll find smashing nightlife, a Unesco World Heritage–listed capital, a beautiful interior dotted with gardens, and wild surf on the lonely east coast, all inhabited by a proud and welcoming populace.
Some two million tourists visit the Cayman Islands each year. Most of them are cruise-ship passengers, who spend a few hours shopping, sunbathing or swimming with stingrays, before pulling out of port. Others hunker down near Seven Mile Beach, enjoying their all-inclusive resort on one of the Caribbean's most beautiful stretches of sand. And a lucky few venture further.