Jamaica's Coolest Boutique Hotels

True confession: I’m a sucker for Island Outpost’s hotels. Their compact collection of Caribbean roosts are right up my alley – funky-cool and fashionable, eclectic and fun. But all this chic has a price, of course, and a stay is hardly a bargain. BUT IO recently announced some summertime specials at three Jamaican hotels that just might put a glamorous getaway within your reach. The Caves

credit: islandoutpost.com

Secreted behind the big blue gates this ultimate high-style/low-key getaway has a dozen cliffside cottages overlooking Negril’s turquoise seas. Make like previous guests Naomi Campbell and Kate Moss and spend your days sipping champagne in a bathtub carved into the cliff, have a romantic candlelit dinner in a cave, or simply sprawl in the oceanfront spa. The biggest surprise at this tiny resort: it’s all-inclusive!

Book the “Escape to Romance” package for a stay May 1-October 31 and save 30% off winter rates. Includes four nights accommodations, food and beverage, private caves dining experience, private caves hot tub experience with champagne, and your choice of a full body massage or brown sugar scrub. Package rates start at $2,458 plus 20% tax and service.


Strawberry Hill



More than 3,000 feet above Kingston, this coffee estate-turned-resort in the Blue Mountains’ hamlet of Irish Town is cool in every sense of the word. From the celeb-studded guest list (Grace Jones and the Rolling Stones slept here; Bob Marley wrote “Natural Mystic” here) to its cluster of gingerbread cottages with four-poster beds dressed with heated mattress pads that temper the nighttime’s mid-50-degree chill, Strawberry offers a completely unexpected Caribbean experience. Who’d ever have imagined that I’d be in Jamaica, quaffing a pre-dinner Blackwell rum punch while comfortably cozying up to a roaring fire?

The Discover the Blue Mountains package gives guests almost 25% off winter rates for stays May 1 – October 31. The three-night stay includes two hikes (on Gordon Town Trail and on Settlement Trail), breakfast, fruit and cheese welcome amenity, dinner with a bottle of wine, daily Blackwell Rum cocktail, and a choice of a full-body massage or hydrotherapeutic coffee scrub. Package rates start at $1,237 plus 20% tax and service.


GoldenEye is an estate once owned by James Bond creator Ian Fleming, now transformed into a 20-suite beachfront hotel at Oracabessa, just east of Ocho Rios. The chic boutique has welcomed celeb guests including the Clintons and Martha Stewart, who have planted trees in the property’s lush grove. Nurse a Red Stripe in the too-cool-for-school seaside Bizot Bar, or pilot a paddleboard along the emerald lagoon.



Just don’t leave without taking a peep at the villa for which the hotel is named, where the desk at which Fleming’s suave spy sprang to life overlooks the garden and a lush outdoor bathroom with a clawfoot tub is the definition of rub-a-dub romance.

Guests who book the “For Your Eyes Only” package for stays May 1 – October 31 save 33% off winter rates. Includes picnic at Firefly (Noel Coward’s historic hilltop estate), 90-minute in-room couples’ massage, guided kayak excursion, sunset cocktails aboard the “GoldenEye” (glass-bottom boat), and four-course dinner with a bottle of wine. Nightly rates start at $560 plus 20% tax and service.