Moonshadow is our pad for the week. It’s a festively painted and rustically decorated wooden cottage with a cute kitchenette, a naughty outdoor shower and a balcony off the upstairs bedroom that soars over the Caribbean like the crow’s-nest on a pirate ship. It’s one of only a dozen one- and two-bedroom cottages at this most unusual waterfront all-inclusive hotel, and it has a distinct energy to it. Not a ghostly kind of energy, but a character-in-the-adventure vibe, the kind that prompts you to write a love letter to it in the guest book by the front door and mention it by name in conversation, rather than just saying “my room.”
Upstairs bedrooms, to quote the management, are “naturally ventilated,” which means no air conditioning, vaulted ceilings and louvered windows all around. Let’s just say it’s a good way to get to know your fellow Cavers, who may be blushing at breakfast. And what a breakfast it is. Nobody does the morning meal quite like Jamaicans, and the kitchen at the Caves doesn’t disappoint. Ackee and saltfish, callaloo and bammy, and a pile of sweet local fruits with fanciful names like naseberry and custard apple. Superb. Eat up; they don’t serve this stuff at Denny’s.
The Caves, just down the coast from Negril’s famous Rick’s Cafe, is named for the immense grottoes that open up below the limestone cliffs atop which it is perched. There’s no beach here, but there is some of the world’s most astonishing water. It’s warm and transparent and bristling with fishes of all sorts. And at key spots along the clifftop, cutouts in the stone wall reveal small platforms from which the brave can leap into space and — 30, 40, 50 feet later — plunge into the sea. Be one of those people. March back to Moonshadow, don your swimsuit and stride confidently to the nearest chink in the wall. Now: One ... two ... three! —Matt Phenix
From $445, 800-688-7678; islandoutpost.com
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From $218, 800-544-2883; theromanticholiday.com
If you loved The Caves, you'll love...
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From $345, 888-334-7609; montpeliernevis.com
Cocos Hotel, Antigua Twenty-six wooden cottages (with showers open to the sea) cling to a rocky outcrop on the island’s west coast. There are white-sand beaches to the left and right, as well as a spa, restaurant and beach bar to keep you relaxed, well-fed and pleasantly pickled.
From $430, 268-460-2626; cocoshotel.com
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From $247, 866-527-4762; hiddenbeachresort.com