Does any traveler really need 14 plasma-screen TVs and a private chef? Maybe not, but Anguilla is luring the St. Bart's crowd with some outrageous indulgences. Douglas Cooper investigates.

Anguilla has never been famous. A small, eel-shaped island in the Caribbean—anguilla means eel in Italian—this British territory has always been overshadowed by its neighbors, especially glamorous French St. Bart's. While St. Bart's has long been a tabloid celebrity, Anguilla was the nice guy whose name you can't quite remember.

That is beginning to change. Along with astonishing beaches—there are more than 30 of them, the color and purity of expensive stationery—Anguilla now has equally astonishing new resorts and an energized restaurant scene. Without much fanfare, the island has become the place in the Caribbean for an heiress to rent a fully staffed private mansion and stuff it full of fab friends. The airport was expanded earlier this year so that the likes of Brad Pitt and Jennifer Aniston (back when they enjoyed each other's company) could land here, instead of arriving by ferry from St. Martin. Denzel Washington recently vacationed here, as did Uma Thurman, and so did Beyoncé Knowles and her beau, Jay-Z.

Until recently, the most coveted rooms on Anguilla were found at three posh Mediterranean-inspired resorts: Malliouhana, which opened in 1984 and has an enormous spa and renowned wine cellar; Cap Juluca, which followed in 1988 and is widely considered the island's finest property; and CuisinArt, which launched in 1999 with white stucco and sky-blue domes. But competition now comes from the growing number of absurdly luxurious villa retreats. Among the most ambitious is Altamer, a modernist complex consisting of three villas named for gemstones. The Russian Amethyst launched first, in 2000; the Brazilian Emerald followed in 2003; and I stayed at the newest, the African Sapphire, which opened last fall.

Carl, my Altamer butler, cheerfully guided me through the 14,000-square-foot pleasure dome, decorated with objets d'art from Algeria to Zimbabwe. He demonstrated the electronic toys: the 14 plasma-screen TVs; the sound system with 35 speakers dispersed throughout the villa; the 30,000 MP3 songs ready to be piped into any of the eight bedrooms, nine bathrooms or gym. A whirlpool bath floats on a bridge that stretches across a private swimming pool. The price for all this? Twenty-five grand a week in low season ($44,000 when you have to compete with people like Brad and Jennifer).

Altamer's chef, Maurice Leduc, who has worked at Maxim's in Paris, presides over the restaurant—which has tabletops made of sea glass and a terrace that looks onto the ocean—and prepares private meals for guests to eat in their villas. He does astonishing things with local crayfish, grilling it and serving it with creamed leeks and plantains; coats grouper with macadamia nuts, pistachios and pine nuts; and spikes his chocolate soufflé with Pyrat rum, an Anguillan blend.

Those lucky enough to be spending the night at Altamer after one of Leduc's dinners can then retire to their villa for a game of billiards on the custom-made table in the living room or a midnight tennis match on one of Altamer's two pristine courts.

Decadent as it is, Altamer has some seriously opulent competition. St. Regis is in the process of expanding its Temenos resort, which opened in 2002 with three luxury villas. Soon there will be 16, with a hotel, spa and several estate homes to join them over the next two years. And, in defiance of Anguilla's parched interior, this sprawling retreat will soon have an equally sprawling 18-hole golf course (the island's first), designed by Greg Norman.

Temenos's design is about rationalist purity, all proportion and perfect detail. Floors are light marble; Romanesque arches and barrel vaults are Mykonos white. I stayed at the Sea Villa, which rents for $33,000 a week in low season ($60,000 in high season) and has five glorious white bedrooms, punctuated by ocean-blue bed linens. There are five bathrooms too, the largest of which—with its marble pillars, sunken marble bathtub and outdoor shower behind a remote-controlled scrim—is just slightly larger than your average two-bedroom apartment in Manhattan. The cathedral-like living room looks out over a private infinity pool, which in turn looks out over a gorgeous beach and an even more infinite sea.

All very impressive, but if you really want to test a resort, get sick there. I try to do this whenever possible. Running a fever? You'll know whether that bed is truly comfortable. Feeling irritable, listless, pathetic? You'll discover the true nature of the staff. After a few days of windsurfing and ocean kayaking on Anguilla's calm waters, I decided to get sunstroke at Temenos. Jamal, my suave, efficient butler, had been doing a stellar job; I figured it was time to throw a curveball. Jamal performed a more than credible nurse impersonation, checking in on me frequently and bringing me water and medication. The gadgets in my villa, albeit not as high-tech as the ones at Altamer, eased my recovery: Soon I was well enough to send e-mails from my laptop in bed. I worked my way up to the living room's flat-screen plasma TV.

In no time I was restored sufficiently to investigate Anguilla's restaurant circuit, which includes some of the best spots in the Caribbean.

Anguilla's best-known restaurant is likely the 11-year-old Blanchard's, an intimate space with a menu of local seafood like lobster and mahimahi prepared in unfussy ways. Owners Bob and Melinda Blanchard have just completed a new cookbook, Cook What You Love, which is in stores this month.

Last November, KoalKeel, a beloved seaside dining room in an 18th-century plantation great house, whose roof had been damaged during hurricane Lenny in 1999, reopened after a renovation. Chef Gwendolyn Smith, an Anguilla native, offers a menu that merges local and international influences: Sharing the roster with traditional Anguillan rice 'n' peas are tandoori lobster and duck glazed in maple syrup.

Then there's Santorini, the main dining room at the CuisinArt resort. Owned by the company of food-processor fame, CuisinArt launched six years ago as a culinary-themed retreat, with a goal of offering superb cuisine along with cooking lessons. But though the resort was a success from the beginning, the kitchen disappointed. Who goes to the Caribbean to eat beef Wellington?

In the last year, however, CuisinArt's kitchen has been transformed under the new leadership of chef Daniel Orr, formerly of Manhattan's Guastavino's. Since his arrival, he has been on an Alice Waters�like crusade to emphasize local ingredients. He hired agricultural experts to help him create an organic garden to supplement the resort's hydroponic farm, and has planted everything from buttercrunch lettuce to chervil. At Santorini, I tried his chilled golden vegetable bisque, made with herbs from the garden, and snapper in a pungent ginger, key lime and chile broth.

I came with higher expectations for the restaurant at Malliouhana, whose wine cellar is—along with Graycliff's in the Bahamas—the most exalted in the Caribbean. Twenty-five thousand bottles represent more than a thousand unique wines culled from around the globe by sommelier Albert Lake and owner Leon Roydon. Unfortunately, though overseen from afar by French celebrity chef Michel Rostang, Malliouhana's dining room delivers merely credible French cuisine, at a price where I expect my life to be altered.

Tasty's, a jaunty little aqua-and-lavender restaurant, proved a far more profound culinary experience. Albert Lake had told me that French celebrity chefs Guy Savoy and Paul Bocuse lunched here. Tasty's is owned and presided over by Dale Carty (who in fact trained under Michel Rostang). Dishes are simply prepared: I tried a perfect marinated conch salad and a remarkable pumpkin soup sprinkled with cinnamon. Sauces are flavored with mango or a spiced banana rum.

While it's easy to eat incredibly well on Anguilla, it's not easy to do so on the cheap. Even at casual restaurants, bills here tend to skyrocket. This isn't likely to change anytime in the near future. Still, it will soon be easier for the chic submillionaire to visit. This fall, Cap Juluca's founders are opening Ku, a boutique hotel on Shoal Bay East that will be more affordable, if not quite cheap.

The big question is whether Anguilla will manage to grow ever more desirable each year while staying wonderfully obscure. My sense is that Anguillans would like that to happen—to be known only by those in the know, to be famous only among the famous. It's a difficult balancing act. For the moment, however, they're doing just fine: They're the swank club in the Caribbean with no sign on the door; if you didn't know it was there, you'd just sail on by.

Douglas Cooper lives in San Miguel de Allende, Mexico, and has written for New York and Rolling Stone.