Nothing is better to visit and nothing is worse to own than a private island. Fortunately, there are plenty of them to rent in the Caribbean, which obviates the hassles of ownership—think Richard Branson riding out Hurricane Irma on Necker, the island he bought for $180,000 in 1979.
But not all private islands are created equal and, ironically, the more private they are, the more hassle it often is to rent them.
“Mustique and Jumby Bay are private, but you’re still sharing them with other people, and then there are islands that are only big enough for small parties,” says Sienna Charles founder Jaclyn Sierra India. “Sometimes, the island’s so private it isn’t fully staffed, or the accommodations aren’t up to snuff. It’s similar to renting a yacht or a huge estate. If some billionaire owner puts their heart and soul into it, and it’s up to highly exacting standards, it’s obviously going to be a better experience.”
The perks also vary widely.
“It depends on the purpose of the trip,” says Luca Fella of Black Tomato. ”Moskito [Branson’s other island] has lots of activities and things to do. For a more barefoot, low-key getaway, we might suggest Petit St. Vincent.”
In choosing an island, an important factor to weigh is the difficulty of getting there. While Fella says that seclusion is “often the whole point,” India maintains that more of her American clients are traveling to the Caribbean for shorter getaways or long weekends, making convenience paramount. Security also plays a role. A more remote island might offer privacy but also lack the infrastructure to make staying there feel safe.
With all these factors in mind, we’ve assembled a round-up of private islands paradises and painted a thumbnail sketch of each, to try and steer your inner Goldilocks to the one that’s just right for you.
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Calvigny (Grenada)
Image Credit: Courtesy of Calvigny This slice of paradise offers total privacy because it requires a full buyout. One widely circulated rumor says that one of Silicon Valley’s biggest tech moguls retreated here for four months while hammering out his divorce agreement. The design aesthetic is barefoot beach house on steroids, and Michelin-starred chefs create feasts using produce from the island’s organic farm and fresh fish from the boats that pull up to the dock daily. Trainers and wellness professionals are on call, as well as spa and beauty technicians. Twenty-five suites and cottages are spread across the island’s 80 acres, all situated on one of three white sand beaches. Outdoor running trails, a state-of-the-art gym, and a tennis court balance out the full complement of aquatic activities, but another option is listening to the wind in the palm trees from the comfort of a hammock. A concert grand piano and easily arranged fireworks help mark special occasions. It’s literally like rubbing a genie’s lamp, except you get more than three wishes.
Rates start at $51,000 per night and go up to $129,000 per night
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Cayo Espanto (Belize)
Image Credit: Courtesy of Cayo Espanto This tiny atoll three miles from the bustle of San Pedro couldn’t be more conducive to romance. It literally specialize in special occasions, with two attentive and dedicated butlers per villa, who will set up a stargazing bed at the end of your private dock (a Champagne bucket within reach), outdoor movie screens to watch your favorite films en plein air, and elaborate, flower-strewn sand sculptures to beautify the superb meals served in and around your isolated little hideaway. The entire resort consists of six waterfront villas, with private pools and docks where guests are picked up for daily excursions to some of the most pristine snorkeling and diving spots in the world. There are no common areas, and the only neighbor you’ll be aware of is Leonardo DiCaprio, whose island is visible in the distance on a clear day.
Nightly rates start at $2,095 and go up to $2,795, although holidays and high season can be higher. Buyouts begin at $16,995 nightly and go up to $23,495 nightly for holiday season.
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Ambergris Cay (Turks and Caicos)
Image Credit: Courtesy of Ambergris Cay Private jets can land directly on the island because the runway has a customs office, and homeowners include Viacom heiress Shari Redstone and the media-baron Hearsts, while the rental pool ranges from one-bedroom beachfront bungalows to six-bedroom villas. The central beach is stocked with toys like Hobie cats, a giant chessboard, and water trampolines, and the Club House has billiards, ping-pong, arcade games, and a shady verandah on which to sip a rum drink. The Caribbean’s only floating Tiki Bar, meanwhile, attracts a fun-loving crowd. The gym building is topped by an open-air yoga pavilion, and there are the obligatory tennis and pickleball courts, as well as waterfront massage bungalows. E-bikes are available for exploring the island, which looks like someone transported the dunes of Nantucket to the tropics. There’s a lookout point for spotting whales, as well as guided birding and nature walks. In short, a smorgasbord of diversions.
All-inclusive nightly rates begin at $2,640 and go up to $14,500. Buyouts aren’t possible, because some of the private homes are not part of the rental pool.
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Guana (British Virgin Islands)
Image Credit: Courtesy of Guana With the tagline “the virgin island that still is,” it’s not surprising that visitors at this large and rustic but luxurious property off Tortola are usually return guests—and often beg newcomers not to tell anyone about it. There’s a strong Robinson Crusoe vibe: discreet cottages and villas tucked into the hills, 12 miles of hiking trails, secret coves, five spectacular beaches (one with food and beverage service), and a central area for socializing that looks like your wildly rich great-aunt’s house in Palm Beach. Not surprisingly, it belonged to a Boston Brahmin family for generations before being purchased in the 1970s by commodities trader Henry Jarecki. A five-acre orchard provides much of the produce. Tennis courts, a croquet lawn, and the Hybiscus Spa are other amenities, as are excursions like Norman Island, the inspiration for Robert Louis Stevenson’s Treasure Island. ‘Nuff said.
All inclusive rates start at $995 and go up to $6,430. Buyouts start at $34,600.
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Aerial (British Virgin Islands)
Image Credit: Courtesy of Aerial (British Virgin Islands) Every visit to this diminutive but luxurious health and wellness retreat benefits Aerial Recovery, a non-profit dedicated to combating human trafficking, aiding veterans, and responding to natural disasters, while the island itself is home to Redemption Ranch, an animal rescue shelter. It’s all part of the owner’s mission to create “the most impactful resort on the planet.” The island’s design mimics a Nautilus shell, with the main hilltop guesthouse at the center. The “One Love” vibe means meals are served communally, with superb pescatarian-forward, locally sourced food—who knew a dessert sweetened with dates could be so decadent? The infinity pool boasts one of the best views in the BVI, and the beach has an outdoor gym, a yoga pavilion, and an open-air cabana for spa treatments. Bonus points for the amphibious boats straight out of a Bond film.
Room only rates range from $625 to $1,750, all-inclusive rates from $1,250 to $3,894, and buyouts start at $25,000 per night.
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Nayara Bocas del Toro (Panama)
Image Credit: Courtesy of Nayara Bocas del Toro Hidden away in an unspoiled archipelago a mere 45-minute flight from Panama City, Bocas Town has begun to appear in travel magazines as one of the most charming small towns in the world. From there, a half-hour boat ride brings you to a mangrove covered island with a central dining pavilion transported from Bali, overwater villas with private swimming pools, and treehouses straight out of Swiss Family Robinson (except with giant copper soaking tubs and futuristic oval doors that swing on a central hinge). The world’s first “aerial beach on stilts” fronts a placid lagoon. Its commitment to sustainability aims for “zero kilometers” of distance between produce and kitchen, and there’s a full-service spa that also offers in-room treatments. Excursions not to miss include a sunset dolphin cruise, castaway lunch, visits to a starfish sanctuary, Sloth Island, and a sea turtle nesting ground. As close as you can get to feeling like Thurston Howell III.
All inclusive rates start at $1,334.80 for an overwater villa and $1,220 for a treehouse; buyouts from $29,710 to $43,150.
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Lovango Cay (U.S. Virgin Islands)
Image Credit: Courtesy of Lovango St. Thomas is an easy flight from most major U.S. cities. Once there, it’s a 10-minute ferry ride to this chill resort with sister properties on Nantucket and Martha’s Vineyard. The same New England sensibility is reflected here, with its unpretentious, toes-in-the-sand tempo. If you think glamping is an oxymoron, think again. The luxury treehouses, villas, and tents are equipped with all the 5-star amenities, not to mention jaw-dropping views. A cluster of Caribbean huts form a mini-mall selling luxury goods, while the Beach Club (which attracts sailboats and day-trippers) is the center of the action, with a swimming pool and bar area. On the other side of the island, Crescent Beach offers solitude and snorkeling, while the beaches of St. John are only a boat ride away. Three-year-old Lovango has already become known for its Food Festival in May, which has attracted chefs like father of poke Sam Choy and Chopped star Tiffani Faison, but the food is equally good the rest of the year, and best of all? U.S. citizens don’t even need a passport.
Rates excluding meals and drinks start at $995 per night for a glamping tent, $2,750 per night for the 3-bedroom villa, and buyouts start at $150,000.
