Beach? What beach?! If you think that the best Caribbean resorts are all beachfront, think again. While I won’t deny the appeal of staying steps from a powdery scallop of sand, there’s a lot to be said for ascending to a hillside haven with panoramic island views. If you or your clients are ready to swap sea level for sky high, check out these off-the-beach oases.
Strawberry Hill, Jamaica When I lived in Jamaica, this intimate spot in the mountain village of Newcastle, 3,000 ft. above Kingston, was the place for weddings and Sunday brunch. Decades later, the appeal of this remote Blue Mountain boutique endures. Owned by Island Records founder Chris Blackwell, the estate has long been a favored spot of musicians (this is where Bob Marley convalesced after his 1976 shooting), but you don’t have to be a star to feel at home here. Set in lush gardens, a dozen fretworked colonial-style cottages offer a warm welcome, and the stunning infinity pool overlooking the capital just begs you to dive in.
Secret Bay, Dominica This Nature Island retreat has been on my list since it opened, and I’m determined to visit this year, now that there are (finally!) direct flights from Miami. I want to experience for myself what it’s like to hole up in plush “treehouse,” complete with its own plunge pool and outdoor shower, my every wish fulfilled by a solicitous villa host. I want to wake up to birdsong trilling from the trees on the mountainside retreat. And if I choose to desert my mountain lair for a quick dip, I’ll only need to ask my host to take me down the hill to one of two petite coves below.
Ladera, Saint Lucia I’ve stayed at this honeymooner’s favorite many times, so I’m confident you won’t miss being at sea level when you’re cosseted in your suite at this ‘Lucian bolthole. Ladera pioneered the three-wall suite concept 32 years ago, and the experience of waking up to the sight of your plunge pool framed by the majestic Pitons and the shimmering Caribbean 1,000 ft below is part of what makes staying at this romantic, 37-suite hideaway so special.
Le Carl Gustaf, St. Barts On my last trip to St. Barts I stayed at this hotel, which sits among the red-roofed hillside buildings overlooking Gustavia’s iconic, yacht-filled harbor. Since then, it’s been sold to new owners, who renovated its 21 suites and villas, some of which feature plunge pools (complete with aqua bikes), all with balconies that offer postcard-perfect bay views. Other highlights: The tiny, tech-forward Spa Diane, and electric bikes and an electric Mini Moke for island adventuring
Montpelier Plantation & Beach, Nevis Princess Diana retreated to this secluded inn with her young princes back in 1992 after her separation from (now) King Charles. Hopefully you’ll find a happier reason to visit this historic sugar plantation-turned-hotel, where a clutch of simple cottages sits in the shade of tropical trees, and you can enjoy a romantic diner a deux in a sugar mill. And, in case you were wondering, lounging by Montpelier’s distinctive black-and-white, mosaic-tiled pool isn’t an indulgence; it’s a requirement.
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