The Caves

It’s okay; just work your way up, I thought, as that old familiar fear began squeezing my internal organs like a bellows. It helped that there were people watching, and the sun was shining, and the water below me was crystal-clear. It helped knowing that many, many others had leapt off these cliffs before me, and many would do so after me, and they probably hadn’t hemmed and hawed like a little wuss, so why not just get on with it? I took a couple steps back to gain momentum (and stall for another precious half-second), performed some version of a run, but more of a shuffling hurl, and then I was out over nothing, and then I was falling forever. 

Perched on and built into one of those cliffs is The Caves by Island Outpost, one of several Jamaican properties owned by Island Records founder (and Wailers discoverer) Chris Blackwell. It comprises 11 breezy one- and two-bedroom cottages, as well as one large villa, all seated on 10 acres at cliff’s edge. With the sea on one side and high walls everywhere else, The Caves are private without being cloistered. A web of paths laces the property, and, for those less nautical, freshwater pools provide respite from the Caribbean heat. 

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Also heat tempering? The rum cocktails shaken up at one of several bars on-site. Cool off after a snorkeling session off the cliffs, or listen to live music while enjoying fresh Caribbean seafood dishes under the stars, or by candlelight and swirling surf in the stunning Blackwell Rum Bar, carved out of two limestone grottoes at sea level. 

But the sea is the star here. Descend down any one of the winding staircases hewn from the cliffs and you’ll end up at a small ledge 10, 20, 30 feet above the water. Which brings us back to the present moment, in which I was plunging, plunging, plunging 10 feet from the cliff’s edge into the tourmaline waters below. I hit the sea with a walloping kind of smack. Up I surfaced, laughing hysterically—really, it was a little disconcerting—and swam back to the cliffs, knowing I’d have to ride this adrenaline off the 20-foot drop, gripping anxiety be damned.

Details: Rates range from $640 to $2,010 per night during high season (January 8-April 30); $480 to $1,480 per night during low season (May 1-October 31). Contact: 

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