If you need to be told why you should go to the Caribbean for a winter vacation, you definitely need the time off. (Fine, here's a quick review: sun, sand, warm water, rum.) The thing is, there's the Caribbean and there's the Caribbean. We refer, of course, to the Caribbean of tacky cruise ships, bland multinational chain hotels, and dropout baby-boomer Parrotheads slurring the words to "Margaritaville" versus the Caribbean, of, well, class. What you'll find below are four of the classiest destinations in the islands. These aren't the places that were making waves last year or the year before, either; these are the It destinations right now.
The Caves, Jamaica
Beneath the hot tub are the cliffs, and beneath the cliffs are the caves, the surreal underground maze of grottoes for which this tiny resort was named. But let's get back to that hot tub, shall we? Rum punch in hand, you sit and soak and look out over Jamaica's western coastline, soaking up the sunshine, listening to mellow reggae drift on the wind.
The Caves has become the place to stay in Jamaica. That's partly due to the setting, partly due to the exclusivity (it's made up of only 12 villas), and partly due to the guest list, which includes the likes of Naomi Campbell, Kate Moss, Jude Law, and Harrison Ford. Beyond all that, the reason people who could go anywhere flock to this resort is because it's rustic, simple, and effortlessly cool. A cliffside ladder, for example, offers direct access from a swimming pool to the ocean. And the laid-back rooms are outfitted with hand-carved furniture, batik fabrics, one-of-a-kind artwork, and a stereo complete with a CD library. And you can bank on the fact that the music in that CD library won't suck. Before he opened the Caves, owner Chris Blackwell started a little company called Island Records.
Details: From $425 per night; 800-688-7678.
Carenage Bay, St. Vincent and the Grenadines
Carenage Bay resort, all pastel and palm thatch, wraps around a small cove, the only thing between it and the ocean being a huge horseshoe-shaped pool. But that in itself hardly distinguishes it from hundreds of other vacation destinations in the Caribbean. So consider the following: Carenage has its own casino and golf course. The bathroom amenities are by Bulgari, the linens by Frette. Guests can cruise the surrounding seas in sailboats or powerboats, or they can toodle around the 800-acre property in golf carts. And while most Caribbean resorts serve up island-fusion cuisine (read: overwrought grouper-and-mango concoctions), Carenage Bay chef Luigi Bergeretto is an Italian magician who imports fresh ingredients directly from the motherland.
Finally, although you may never have heard of the prestigious Five Star Diamond Award (it's handed out, not at all readily, by the American Academy of Hospitality Sciences), Carenage Bay is the one and only property in the Caribbean ever to receive it.
Details: From $360 per night; 784-458-8000.
Ocean Club, Bahamas
Unlike many voguish Caribbean resorts, the Ocean Club is neither quaint nor a hideaway. It is grand and luxe and sweeping, with terraced gardens modeled after those at Versailles. What's more, the Ocean Club has just undergone $100 million in renovations, and whatever you may think about quaint hideaways, it's extremely tough to argue with a redecorating bill of those proportions. It's also tough to argue with Cindy Crawford and Michael Jordan, both of whom have deposited their famous selves at the Ocean Club for a stay. (Jordan will be hosting the inaugural, and humbly named, Michael Jordan Celebrity Invitational golf tournament at the resort in January.) The big-ticket makeover brings 50 new oceanfront rooms, a full-service spa, and star chef Jean-Georges Vongerichten's beachfront restaurant, Dune. And while those quaint Caribbean hideaways may share the same pretty beaches and turquoise waters, they certainly don't offer butler service, Internet access, or in-room DVD players.
Details: From $400 per night; 800-321-3000.
Parrot Cay, Turks and Caicos
For that one week each year when an executive feels not only deserving of but justified in turning his back on clients, colleagues, and commitments, there is Parrot Cay. The 1,000-acre property on Turks and Caicos (head south from Miami, hang a left at Cuba) is only accessible via boat, and simply put, it's the perfect place to relax under a Caribbean sky and an assumed name.
The solitude-seeking traveler will find tennis, mountain biking, windsurfing, waterskiing, scuba diving, a 6,000-square-foot spa, and an "infinity" pool, which creates the illusion that the water blends right into the ocean. On the off chance that deep, spiritual peace is the goal, there are yoga instructors, a private meditation garden, and a spa treatment called a Balinese-spice body mask, which, while not strictly spiritual in nature, certainly couldn't damage your karma.
Parrot Cay's 56 cottages-each has a veranda, terra-cotta floors, and a big four-poster bed-are lovely. But if you've got money to incinerate, book yourself into the Pirate House, the home of Parrot Cay's owner. It has two and a half bedrooms, the best vantage points on the island, and a private-very private-pool.
Details: Cottages from $645 per night, Pirate House from $2,300 per night; 877-754-0726.
