What are the best hotels in the Caribbean? I’ve had the good fortune to have spent much of the past 25 years romping around this compelling region, so have hundreds to choose from – though of course my wicked mind goes immediately to the worst ones.
There was the Four Seasons Resort where, when I asked for brown toast at breakfast, they brought white with the glib comment “don’t worry, sir, we’ve cooked it a lot”. And the place in Antigua where the spa therapist refused to give me a massage because I asked for the air conditioning to be turned off. “I can’t work if it’s too warm,” she said emphatically. Or the “characterful” place in St Lucia where the mosquitoes made night-time bathroom trips a dash rather than a stroll.
Yes, there can be duds, but the abiding joy of hotels across the Caribbean is that you’re rarely far from a gorgeous beach where the warm, turquoise waters are all the more delightful for the winter woollies you know everyone back home is wearing. Gardens come with radiant flowers and hummingbirds as standard, and staff often go above and beyond. I fondly recall the chef who took us to see turtles hatching on a moonlit beach, the general manager who liked to go hiking with his guests and the old bartender who showed me how to make the definitive rum punch, topped with grated nutmeg.
In whittling down my top 50 hotels, which are sprinkled across 27 islands and territories from the Bahamas to Tobago, I’ve selected standout properties for all occasions – classic and contemporary, family and boutique, luxury and affordable. If all-inclusive resorts appeal, head for Barbados, Antigua or Jamaica; for small and characterful places aim for Grenada, Nevis and the Grenadines; to avoid hurricanes, go Dutch in Aruba, Curaçao and Bonaire. For a push-the-boat-out treat it has to be St Barts or Anguilla. Note that some places close in autumn. Many hotels have been upgraded post-pandemic; all are primed to welcome us with big smiles.
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