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On the still-bucolic site of a former coconut plantation just west of Montego Bay, Round Hill is another of the legendary hotels created in the early 1950s to accommodate wealthy Brits and Americans who were discovering the pleasures of a Jamaican winter. Since then, it has evolved into a thoroughly modern resort that manages to retain its original, exclusive, clublike spirit. In the beginning, Round Hill consisted of a group of shareholders (British playwright Noel Coward was one) who rented out their private villas when they were absent. That’s how it still works, although the celebrity shareholder most mentioned these days is designer Ralph Lauren, who rents neither of his two villas. Along with 27 other villas, which can be divided into 86 suites, there’s the Pineapple House, a seafront block of 36 rooms, all decorated, predominantly white on white, by Lauren. The ambience is quiet luxury, the service is relatively formal (the doorman wears white), and the children among the guests are treated as the heirs and future holiday decision makers that they are. Almost every villa has a story, whether it has to do with Coward, the Kennedys, or How Stella Got Her Groove Back. And Montego Bay, whose city lights can be seen only from the highest villa (#28), is still another world away.

Some 35 minutes by boat from Providenciales, sitting all alone on a 1,000-acre island with three miles of white-sand beach, Parrot Cay attracts a seriously moneyed clientele who care, more than anything, about its exclusivity and its spa. Parrot Cay is not exactly monastic: the long list of celebrity visitors has included Jennifer Garner and Ben Affleck (they got married here), as well as Paul McCartney, Julia Roberts, Jerry Seinfeld, and Liam Neeson. But the spa, COMO Shambhala Retreat, is so successful at projecting a holistic way of life that a sense of peace and harmony embraces the entire resort. The central garden-view and ocean-view rooms, three minutes’ walk from the beach, are acceptably chic, but the beachfront suites and villas are knockouts, and the handful of private homes for rent, some owned by celebrities (Christie Brinkley, Donna Karan), are in the fantasy category. The food, by a chef whose résumé includes a Michelin star, and the service, performed by private butlers for some room categories, are of commensurately high standards.

Kimpton Seafire Resort + Spa, a Seven Mile Beach favorite on Grand Cayman, combines luxury with sustainability. Here, a 143,000-watt solar array (among the largest in the Cayman Islands) generates electricity. The hotel also harvests rainwater for landscaping and uses aluminum water bottles instead of plastic.

In addition to being family friendly—it has a great kids camp—Seafire is animal friendly. For example, it has special outdoor lighting to prevent distractions for the local turtle population, who use moonlight to guide them to the sea. The property also has trained a group of local divers, deemed “Seafire Guardians,” to help with local coral reef regeneration. The resort’s commitment to the area’s wildlife makes it ideal for travelers looking to support the island in a responsible way.

If you want to vacation like British royalty, visit the mosquito-shaped island of Mustique, which Naomi Campbell, Mick Jagger, and Princess Margaret have all called their home away from home. Once on land, there’s no better place to stay than the Cotton House, a private retreat that feels like the lap of luxury. Set on 13 acres of cerulean beachfront and gardens thick with jasmine and frangipani, the 20 rooms and suites are awash in neutral hues inspired by their surroundings, with wicker pendant lighting, ikat throw pillows, and breezy mosquito nets over the beds. Explore the coral reefs near the shoreline in a glass-bottom kayak, or improve your backhand with help from the resident tennis pro. After a day of sun-soaked adventure, dine on fresh-caught specialties (pan-seared barracuda, Caribbean-style sushi) at Veranda restaurant, then retire to the Great Room, a colonial-inspired lounge offering rare and local rums.

Fifteen minutes south of the Puntacana Resort & Club, Eden Roc at Cap Cana is the most exclusive of the six hotels in the gated Cap Cana Reserve. At this Relais & Châteaux property, guests have their choice of beachfront suites with kitchens; stand-alone suites with private pools, gardens, and verandas; and oceanfront villas that come with butler service. Whichever you pick, you’ll also have access to an oceanfront infinity pool, a 30,000-square-foot spa and wellness center, and a private, Blue Flag–certified beach. There’s even a kids’ club in a lagoon-side treehouse for when adults need some alone time.

When hunger strikes, head to La Palapa for seafood and Caribbean fare, or Blue Grill Bar + Restaurant for Nikkei and robatayaki cuisine. Should you want to venture off-property, know that Cap Cana is home to an 18-hole Jack Nicklaus signature golf course. Bespoke helicopter outings, visits to the Punta Espada equestrian ranch, and days at Scape Park (a natural theme park with attractions like zip-lining and cave expeditions) can also be arranged.

Opened in 2003, Carlisle Bay is set on a lush, isolated section of Antigua’s south coast and has a 21st-century design that feels more contemporary than Caribbean. With muted shades of grays, whites, and greens, the hotel projects an uncluttered, understated luxury. Its most remarked-on feature, though, is the way it appeals to both couples and families by keeping the two separate. Each group has its own cluster of rooms at its own end of the beach, and never the twain have to meet, except perhaps for lunch at Ottimo, the poolside Italian restaurant. The crescent of beach is tucked into a sheltered bay, so the waves seldom do more than whisper up onto the white sand, against a backdrop of forested hills. It’s all very restful, but the long list of free non-motorized watersports and the extensive kids’ club ensures everyone has plenty to do.

A private-island resort six minutes by boat off the coast of Antigua, Jumby Bay is one of the Caribbean’s top luxury, all-inclusive stays, and one of its most environmentally aware. A $28 million renovation in 2010, which included the addition of 28 suites and a first-ever spa, gave it all the digital-age essentials: 42-inch flat-screen TVs, iPod docking stations, Bose sound systems, free Wi-Fi. Yet its underlying spirit of environmental responsibility, highlighted by its hawksbill sea turtle preservation program and its banishment of wheeled vehicles except for golf carts and bicycles (every room comes with two bikes), continues to reign. Rosewood manages the resort, but it belongs to an association of island homeowners, some offering their properties for rent. So if, say, a 1,346-square-foot beach-view pool suite isn’t big enough, it is possible to do as celebs such as Hillary Swank, Jim Carey, and Paul McCartney have done and plop down up to $20,000 per night for a private villa or estate home. Couples can be perfectly content here, but it is especially attractive to families, who appreciate programs like the Rose Buds kids’ club.

Since its opening along a dazzling stretch of sand known as Cabbage Beach in 1962, The Ocean Club on Paradise Island has been the preferred stay of old-money patriarchs and traditionalists. Though much at the serenely posh resort has remained unchanged, the 105-room property has been modernized to meet today’s standards with spa-sized marble bathrooms, sweeping WiFi, and a restaurant run by star chef Jean-Georges Vongerichten. But it’s the feeling of a privileged, unhurried yesterday that continues to draw an appreciative upper-crust crowd. An on-site tennis pro provides tips for improving your backhand, Versailles-inspired gardens complete with a 12th-century Augustinian cloister offer moments of quiet contemplation, and rounds of golf end with martinis at the resort’s bar. These details, plus knowing that a personal butler and afternoon champagne and strawberries are included in the price, keep guests returning year after year.

Four Seasons might have spruced up the property slightly when it took over management from Viceroy in 2016, but the original clean lines and sharp angles of the midcentury modern architecture coupled with Kelly Wearstler’s playfully eclectic interiors are still unmistakable at this stunning property overlooking Meads and Barnes bays. Epitomizing tropical modern luxury, the property is awash in marble, natural stone, and wood, with dramatic views of the Caribbean Sea from dining rooms and infinity pools that seem to hover from their cliffside perches. Spanning 35 acres, the resort is home to 166 spacious, serene, and stylish accommodations ranging from suites to townhomes and private villas. Indulge at five dining venues, including the aptly named alfresco Sunset Lounge for sushi and the fine-dining Cobà, where fresh seafood is paired with choice cuts of meat and an impressive wine list. With three swimming pools and two distinct beaches to choose from, the most stressful part of the day is deciding where to lounge.

It’s easy to see why Jade Mountain is consistently ranked St. Lucia’s most romantic hotel. Rising high above the sea and offering an unparalleled view of the Pitons, the hotel features adults-only rooms with an open concept (the so-called “sanctuaries” are missing a fourth wall), equally dramatic alfresco baths, and private jewel-toned infinity pools with otherworldly vistas. (The resort was also the backdrop for a season finale of The Bachelor.) James Beard Award–winner Allen Susser prepares the food of love in the on-site restaurant using ingredients cultivated in the resort’s private organic farm, and a rotating schedule of weekly classes, from rum tastings to a tandoori cooking lesson, encourages shared experiences. Guests also have access to the rendezvous-worthy beaches and spa of sister property Anse Chastanet, located just down the hill.

Located on a craggy cliff jutting between Meads Bay and Turtle Cove Beach, Malliouhana has views of the glittering aquamarine sea that will hypnotize guests from the moment they arrive to its chic porte cochere. The bright, cerulean open-air lobby with mirrored mosaic-tile flooring tumbles out to a deck where tiered infinity pools are punctuated by ruffled yellow umbrellas, and a cliffside restaurant serves fresh seafood and farm-to-table fare. Built in 1984, this is Anguilla’s original luxury resort, which reopened in December 2018 after a complete restoration following Hurricane Irma. While guests may find it hard to take their eyes off the dazzling Caribbean, the 46-room boutique hotel’s interior design offers its own portal to the sublime with an aesthetic that can best be described as tropical eclectic. Guest rooms are painted sorbet yellow or robin’s-egg blue and feature white lacquer four-poster beds, mural panels by Haitian artist Jasmin Joseph, Venetian glass lamps, and sea-green marble bathroom vanities. All of this somehow swirls together for a look that’s both regal and untamed. Beyond the rooms, guests can look forward to an extended pool deck with fresh cabanas, as well as the Bar Soleil, which offers a prime spot to watch Anguilla’s famous sunsets.

Mandarin Oriental’s first Caribbean resort has all the amenities you’d expect from the luxury brand—with the price tag to match. Nestled within lush greenery overlooking the white sands of Godahl Beach, the 26 suites and villas, which sit on the grounds of a 1,200-acre estate on the island of Canouan, are elegantly appointed with modern furnishings, marble baths, and rosy accents befitting the hotel’s name. Here, though, it’s all about the public spaces, including a Jim Fazio–designed golf course overlooking sparkling blue waters, a hilltop spa specializing in island-themed treatments, and four elegant restaurants serving every kind of cuisine, from pan-Asian to Italian. At Turtles, a cocktail lounge straight out of the Hamptons, opt for the Pepper Bliss, made with rum, bell pepper syrup, and pineapple juice.

Serenity is easy to come by on the private-island resort of Petit St. Vincent, a 115-acre property from the 1960s. It recently underwent a multimillion-dollar renovation but retains its original charms—there are no cars or in-room televisions (and don’t even think about WiFi) in the 22 cottages and suites, and anything you might need arrives at your doorstep with the simple raise of a yellow flag. A Balinese-inspired spa soothes the body, while two open-air yoga pavilions quiet the mind. If you’re looking for more action, you can explore the island’s pristine reef formations with expert divers through Jean-Michel Cousteau’s only Caribbean scuba center, or rent one of four yachts to catch local mahi mahi—then have the chefs prepare it for you beachside back at the resort.

Digital nomad Wanda Duncan is creating a nurturing environment for women just like her.

No, it’s not the New York Public Library.