Three private-island resorts—hotels that extravagantly claim entire islands for themselves—set the bar for seclusion and discretion. They also have history on their side: each has been in operation for decades.
Buff Strickland

Connoisseurs of the Caribbean who crave an ever-more-exclusive getaway can call off the search. For the Caribbean as you've never seen it—no cars, no crowds—step ashore and join the very happy very few.

Peter Island Resort, British Virgin Islands It is a point of pride with me never to talk to strangers—not in line at the supermarket, not in elevators, and definitely not on vacation. But something about my day on Deadman's Beach had been so pleasant that I didn't pretend not to hear when the couple in the next palapa over called out, gesturing energetically. On this carefree Caribbean day, a soft breeze rustling the palm fronds, I was filled with goodwill.

Honeymooners from New Jersey in their late thirties, Chuck and Lorraine wasted no time in calling me by a diminutive no one has used since I was seven. Lorraine told me they had arrived on Peter Island two weeks earlier with the intention of staying five days. Before they knew it five days had grown to a week, a week to 10 days, and so on. Chuck, who is in the construction business and lives by his cell phone, even called his site supervisor and ordered him to take his number off speed dial. He would not be leaving Peter Island anytime soon. "It doesn't get any better than this, Chris," Chuck assured me, grabbing my shoulder for emphasis.

To quote Smokey Robinson, I second that emotion, for on almost every level Peter Island does not disappoint (no one expects great food in the Caribbean). If you have no experience of private-island resorts but always dreamed of going to one, it offers an excellent initiation, delivering in quantity everything the genre is known for, especially peace and privacy. Add to that a staff-to-guest ratio of two-to-one, atypical service for the region (it's friendly and professional), and five untrafficked beaches (Deadman's is a mile-long crescent of sugary sand).

A 30-minute boat ride from Tortola, Peter Island bristles with vegetation along most of its mountainous, 41/2-mile length. All the buildings are concentrated on 300 of the 1,200 acres, the balance being gloriously undeveloped. The size of the island feels just right: not too big, not too small.

The resort was launched in 1969 with 32 guest rooms in eight prefabricated A-frames shipped over by the founder, an industrialist, from his native Norway. Lorraine said her heart sank when she thought they were going to put her and Chuck in one of the chalets ("in the Caribbean?!"), built away from the action on reclaimed land directly on the harbor.

The rooms you want are any of the 20 junior suites in two-story cottages on Deadman's Beach, added when Amway became Peter Island's unlikely proprietor in 1978. (It is now privately owned by the company's chairman.) Refurbishment of this part of the resort, completed last year, cost $3.2 million, or an impressive $160,000 per unit. While the style of the accommodations is pleasantly safe, bathrooms in cedar shakes and volcanic stone have a high wow factor, with Jacuzzis and showers for two. When the blind is up on the glass wall that separates the stall from the bedroom, you can lather up with a view of Drake's Channel.

Peter Island wears the expensive perfume of exclusivity. As a guest you feel special, privileged. As Chuck put it, "Hey, man, let them eat johnnycakes!"

800/346-4451;; doubles from $615, including meals.

Meridian Club, Turks and Caicos The first thing anyone needs to know about the Meridian Club—and the last thing you are likely to learn about it before going—is that it is not a real hotel. That's not a criticism. It's just the way it is. The Meridian would agree. And, of course, its very un-hotel-like qualities are exactly what many people love about it. Loyalists who have been coming to the resort since it opened 30 years ago wouldn't change a thing. If suddenly it became as well-oiled and systematized as a Four Seasons, they'd be gone in a minute.

Initiates, however, may need time to get their sea legs. The Meridian has a fax but no phone. Other resorts make a lot of noise about forgetting the outside world, but this one means it. You hardly ever see the staff, and the reception desk is almost purely symbolic. Mostly, you're on your own on Pine Cay, which is a 10-minute skip on a puddle jumper from Turks and Caicos's airport on Providenciales. Flat as a debit card, and about the size of New York's Central Park (half of it guaranteed to remain wild), the island has a delicious Survivor-ish feel, minus the aggression.

After two days at the Meridian, I began to understand the resort's laissez-faire appeal. It's contrary to most notions of what constitutes a luxury vacation, but I discovered how liberating it can be not to be fussed and hovered over—even, believe it or not, at the cost of many hundreds of dollars a day. One fashionable school of hotel service kills the client with empty kindness. With its ban on solicitude, the Meridian takes the opposite approach.

If the resort can be compared to anything, it's to an informal—once your shoes come off, they never go back on—country club, which is how the 35 families who have houses on Pine Cay (and are the Meridian's owners) use it. Six low-slung buildings of no distinction house 13 guest rooms whose size and situation make up for what they lack in zing. Set back 100 feet from the shore, each has sleeping and sitting areas, a proper dressing room, open and screened terraces, and indoor and outdoor showers (in a great missed opportunity, the outdoor ones are so lacking in privacy, their appeal is limited to exhibitionists). The only completely private, freestanding unit is Sand Dollar Cottage, which, naturally, everyone wants. There's always a waiting list.

Who goes to the Meridian Club?Collectors of seashells, lovers of desert-island picnics, nature freaks who thrill to the mating of glowworms, and regular people who appreciate a twisted orange slice on their breakfast plate. At dinner—the bell is rung at 7:30 sharp—there is talk of summerhouses on Nantucket and people are still telling lots of jokes at the expense of the Clintons. And though guests can be a boisterous lot, they're all in bed long before midnight.

Pine Cay; 800/331-9154;; doubles from $650, including meals.

Petit St. Vincent Resort, The Grenadines Her name was Geneviève, and she bumped along in her tiny launch from neighboring Palm Island for an hour just to see me. She had a lovely gamine quality. We spoke French. She told me of her childhood on the oyster beds of Brittany. How could I not love her?

In less time than it takes to light a cigarette, Geneviève set up her massage table on the vast terrace of my cottage on a spectacular bluff 75 feet above the sea. There is nothing more boring than a description of someone having his flesh kneaded, so I'll spare you the details, except to say that her brand of tugging, dragging, and pinching is a powerful cocktail of one part Swedish massage to two parts shiatsu. Geneviève knows something the others don't.

An hour may seem like a huge amount of time to ask someone to travel for just one massage, but that's the way things are done on Petit St. Vincent (hereafter, P.S.V.). You want it, you got it has been the resort's M.O. since opening in 1968. Though it's costing you, of course, everyone's willingness to please is a great boost to the ego. I keep a list of things I must do before I die. After my stay on P.S.V. I was able to check off eating grilled lobster in a rope hammock hung in the shade of a palapa six feet from the sea; splashing in the Caribbean with seven golden Labs (they belong to the expat owners); and summoning service, yes, by hoisting a flag. In the absence of telephones, each of P.S.V.'s 22 guest cottages has a bamboo pole planted near its entrance. You want to order room service or catch a ride in a golf cart, you fly the yellow flag. For "do not disturb," you choose red. Every 20 minutes, at least, staffers make the rounds and do a color check. (Don't misread their deadpan demeanor; beneath it, they're extraordinarily sweet.) As a test, I wanted to see what would happen if I ordered lunch, and then immediately put up the red flag. It must have been a difficult decision, but the kitchen honored the system and canceled my meal.

My cottage's perch made me woozy with exhilaration, but I talked to other guests who were just as dedicated to their waterfront digs. (The only ones not to consider are the two-in-one units.) Built of purpleheart hardwood from Guyana and rough bluebitch stone quarried on the island, all accommodations come with two queen beds, two daybeds in the living room, terra-cotta floor tiles, and handsome, crunchy straw mats from St. Vincent. They're scattered along P.S.V.'s two-mile perimeter, which encloses 113 gently hilly acres traversed by concrete paths. Like tidiness?You'll love P.S.V.: the carefully tended plant life is greener than the Meridian Club's, though less luxurious and interesting than Peter Island's. And more so than its competition, P.S.V. has the hushed, protective feel of a sanctuary.

It's a feeling well-earned, considering the effort it takes to arrive. The closest you can get to the resort when flying from the States is Barbados. From there, it's a 50-minute flight to Union Island. From there, it's 30 minutes in a motor yacht to P.S.V.

You arrive wrung out, then call Geneviève.

800/654-9326;; doubles from $585, including meals.

Pieces of Paradise: More Private-Island Resorts

Parrot Cay Turks and Caicos; 877/754-0726;; doubles from $450, including breakfast. Glamorous, even a bit decadent, the 60-room resort of tastemaker Christina Ong has some of the most luxurious freestanding beachfront accommodations in the Caribbean. Just ask Donatella Versace.

Guana Island British Virgin Islands; 800/223-1108;; doubles from $640, including meals. Guana is one of the most intimate private-island resorts: just 15 rooms. It's as much about what you get (food that's better than you expect) as what you don't (phones and televisions).

Young Island St. Vincent and the Grenadines; 800/223-1108;; doubles from $345, including breakfast and dinner. Each of the 30 cottages at this clubby standard-bearer comes with an ocean view and open-air garden shower.

Peter Island Resort & Spa

This private-island retreat is all about serenity and catering to classic desert-isle fantasies. The resort is committed to delivering in quantity everything the genre is known for, especially peace and privacy. Add to that a staff-to-guest ratio of two-to-one, atypical service for the region (it's friendly and professional), and five untrafficked beaches for the thirteen sunny two-story bungalows that make up the property's 52 rooms on 1,800 acres. Elopers are common at this resort, and no wonder: the staff organizes everything before your arrival, leaving nothing for you to do but say, 'I do.' If marriage isn't in the cards, a couple can still take advantage of the countless coves, accessible only by sea. Boatmen will drop you off with just a picnic basket and your imagination. You don't have to be a guest to use the spa, which welcomes day-trippers for the ultimate indulgence: 5 hours of massages and body buffing in a private couples suite.

Petit St. Vincent Resort

After a multimillion-dollar overhaul, the private-island resort reopened in November 2011 with new Balinese touches and a hillside spa. 22 stone-walled, thatched-roof cottages are done up in earthy tones and driftwood palapas now line the beach. There's also a waterside restaurant and a tree-house-style spa, where an open-air hot-stone massage is the perfect end to the day.

Meridian Club

The exclusive Meridian Club edges a two-mile beach on an 800-acre privately owned island named Pine Cay, between Providenciales and North Caicos. The remote, almost isolated, atmosphere promotes relaxation: no cars, no TV, no phones are permitted, no shoes are needed, and no children under 12 are permitted (except during the "family months" of June and July). Guests may stay in one of a dozen dune-side suites (the resort also features a honeymoon cottage and several privately-owned rental homes), each with ceiling fans, large windows, a screened-in deck, and separate bedrooms. The waters off Pine Cay area are renowned for bonefishing and reef fishing, and guests can also arrange active pursuits like sailing trips, snorkeling and scuba excursions, and even golf outings to one of the nearby islands through the resort’s main office.