All travelers dream big, but only a handful can truly afford a six-figure vacation. With its spectacular beaches, resorts and villas that exude exclusivity, the Caribbean is the primo perch for the richest 1 percent who pay top dollar for privacy, plenty of space and spoil-you-rotten amenities. Check out our big-bucks bucket list and live the dream.
The holy grail of extravagance, Round Hill Hotel & Villas west of Montego Bay in Jamaica is a Caribbean classic. Built in 1953, the hotel has long hosted discerning guests like John F. Kennedy, who penned his famous “ask not what you can do for your country” presidential inauguration address in Villa 25. Writer Ian Fleming of James Bond spy novel fame preferred Villa 3. Superstars Beyoncé and Sir Paul McCartney and British royalty like Prince Harry have also checked into the posh retreat. Smartly designed by Ralph Lauren, who owns two of the 27 villas, Villa 20 is built for maximum privacy at the edge of the forest. The six-bedroom, eight-bathroom, two-pool villa measures nearly 9,000 square feet and easily sleeps 14. Nightly rates start at $11,039 through April 22 and $5,679 from April 23 through Oct. 31.
A week at Jade Mountain in St. Lucia is an Olympian-sized treat. Designed by owner and architect Nick Troubetzkoy, its showpiece sanctuaries are sweeping spaces with infinity pools, unapologetically sinful bathrooms and the signature fourth wall that opens to views of the Piton peaks and Caribbean Sea. Check into one of three Galaxy Sanctuaries – the resort’s largest suites – for a seven-night Total Romance package that costs $31,476 per couple through April 15 and $26,856 during the summer. A host of luxe accessories include a bottle of French bubbly, tours of the Diamond Mineral Baths and Sulphur Springs, snorkeling trips, diving class, massages, jungle biking, yacht sails, meals, drinks and a $500 certificate for a return visit. A six-minute helicopter ride from the Hewanorra International Airport goes for $280 per person, one way. By comparison, a taxi takes an hour with a minimal fare of $75.
On Shoal Bay West Beach on the southwest tip of Anguilla, you’ll live like royalty in the Antilles Pearl at the Altamer Resort. Designed by architect Myron Goldfinger, whose work has been exhibited in New York’s Museum of Modern Art, the 12,000-square-foot, five-bedroom villa has a striking geometric chalk-white exterior. Guilty pleasures include an elevator to traverse the three floors, butler service and a 23-speaker sound system. A 50-foot skywalk hovers over the beach and the rooftop terrace features 360-degree views. For the active crowd, there are tennis, basketball and volleyball courts on site. For a few extra dollars, Chef Rexy prepares meals in the gourmet kitchen. Weekly rates start at $42,350 in March, $27,500 in April and $22,500 from May 1 to Oct. 31.
Villa Neo turns up the swagger at the exclusive Eden Rock, the first hotel to open on the French island of St. Barts 60 years ago. Spectacular in design, the six-bedroom villa comes with a cinema, gym, Turkish bath and nightclub. A butler and chef are on hand and for a day in the sun, chairs, umbrellas and a cooler are set up on nearby Eden Rock Beach. Rates for a seven-night stay through April 14 start at $125,000. From mid-April through Dec. 15, weekly rates start at $75,000.
Guests at Eden Rock can take to the high seas – or in this neighborhood, the calm waves – aboard a five-deck superyacht named Joy. The sporty crew includes a fitness instructor, physiotherapist and boxing coach. Joggers can do their thing on the upper deck while the more pensive enjoy a yoga session on the bow. The cabins feature floor-to-ceiling windows. A seven-night slumber party on the open water comes with a price tag of $840,000 in the winter and $700,000 in the summer.
While the beach at Shoal Bay East in Anguilla is the main attraction, a Beachfront Villa Suite at Zemi Beach House Resort & Spa could steal the show. Super-spacious with three bedrooms, there’s plenty of room for a terrace, big kitchen and a pool that overlooks the sea. Get your Zen on in the Thai House Spa where the $305 Sun Ritual is two hours of pure bliss. The Rhum Room impresses with a $90 “Pirates of Caribbean” flight selection with shots of 21-year-old Appleton Estate rum from Jamaica and Mount Gay XO rum from Barbados. For those who like to eat local, lobster at the Stone restaurant is the real deal at $49. Nightly rates through April start at $3,950; from May to December, a sweet stay starts at $3,000.
The beach is just the beginning at C’est la Vie in French St. Martin. On the western tip of Terres Basses – or the Lowlands, as the locals call this area – the six-bedroom, seven-bathroom villa comes with a deck outfitted with a heated pool, Jacuzzi and bar. On Plum Bay Beach, the vacation playground invites with hanging pool loungers, two fire pits, three outdoor showers and a chef serving by the pool or inside the palatial dining room. Nightly rates through April 14 start at $6,286 and at $4,715 from April 15 to Dec. 16. For those booking for the holidays, the villa goes for $12,143 nightly from the middle of of December through Jan. 7, 2020.
Also in St. Martin, the seven-bedroom Sandyline features interiors designed by Philippe Starck, a tropical reef aquarium, grand piano, chef, gym, steam room and tennis court. Massage therapists and tennis pros are extra. Nightly rates through April 14 start at $6,429 while a stay during the holidays in December jumps to $19,500.
Commanding a prime location on the Grand Cul-de-Sac in St. Barts, Le Barthélemy Hotel & Spa is, indeed, grand. For a high-roller stay, Aqua and Bleu are twin oceanfront villas, each with six bedrooms, a wine cellar and lap pool. A chef works his magic in the big kitchen and staff arrange stand-up paddleboarding, kite surfing and snorkeling to see the sea turtles. Steam rooms and vitality pools are in Le Spa although massages are add-ons. Rates for a weeklong stay are $60,500 through April 16 and $41,800 in low season.
Sky’s the limit
If a resort rather than a private villa is more your speed, check into Marigot Bay Resort & Marina in St. Lucia overlooking what author James Michener described as “the most beautiful bay in the Caribbean.” Balanced on a leafy hillside, the majestic three-bedroom penthouse features a four-poster bed, high ceilings, a hot tub and big kitchen. There’s plenty to do like mixing and matching rubs and scrubs at the spa, where new options include outdoor meditation classes and hikes across Marigot Bay Ridge. For foodies, farm-to-fork dining and tastings at the Rum Cave fit the bill. If learning to sail is on the bucket list, a five-day course for $4,000 per person is taught by the pros. For families, gratis funky fun at Zando’s Kids includes coconut bowling and shell painting. The Gros Piton Nature Climb and Swim costs $715 for four. For sunset spotters, a one-hour sail is priced at $200 per couple. Nightly stays in the three-bedroom penthouse cost $1,494 through Easter, $1,116 through the end of spring and $1,314 in June.
The only resort on the petite British isle that fronts two beaches, Four Seasons Anguilla is the pinnacle of posh with a two-story, five-bedroom, five-bathroom villa. With access to Barnes Bay Beach, the villa comes with butler service, a sun deck outfitted with a plunge pool, meals prepared by a chef in the gourmet kitchen, en-suite spa treatments and round-the-clock room service. Nightly stays start at $7,850 through April 30 and at $7,250 from May 1 through Dec 15.
Hey big spender
The fine art of chilling out starts in the six-bedroom villas at The Shore Club in Turks and Caicos Islands, where guests can use an underground entrance to ensure privacy. The palaces in Providenciales are designed with kitchens next to the outdoor dining area and patios that face Long Bay Beach. Concierges and chefs are available for en suite dining, and guests have access to the resort’s pools, spa, bars and fine dining restaurants. Nightly stays through Dec. 19 start at $6,000.
Also in Turks and Caicos, whatever floats your boat you’ll find on the 65-foot catamaran called Kitty Katt. Big enough for 90 and wonderfully private for two, the price tag is a hefty $4,900 for a two-hour sail that stops at a private island for snorkeling and beach time. There’s also plenty to do on board like topping off your tan, finishing the novel you brought from home and cooling off on the waterslides.
Ritzy real estate
In Grenada, the AAA Five Diamond Spice Island Beach Resort is a collection of 64 chichi suites on Grand Anse Beach. At the all-inclusive and family-owned resort, high-rollers go for the Cinnamon and Saffron suites, each with a four-poster canopy bed, Molton Brown amenities in the marble bathrooms and a spacious patio with a hammock. If yoga in the beachfront pavilion isn’t relaxing enough, kick it up a notch at Janissa’s Spa where $180 buys a yummy Chocolate Body Wrap. Nightly rates in the Cinnamon and Saffron suites start at $3,091 through April 15; rates in May, June and July start at $2,155. For golfers, greens fees at the nine-hole Grenada Golf Club are included.
A first in the Caribbean, over-the-water villas at the adults-only Sandals Royal Caribbean in Montego Bay, Jamaica, are about as picture-perfect as it gets. The Tahitian-style watery wonderlands sit on a deck that floats above the Caribbean Sea. Designed with see-through glass floors, the villas also come with hammocks suspended over the water, an infinity pool on the deck and a big soaking tub. Butlers do all the heavy lifting like making dinner reservations at eight restaurants, booking spa treatments and suggesting sightseeing tours. Rates start at $1,541 per person, per night.
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