Inside Kiawah Island, Coastal Charleston’s Private Preppy Paradise

Inside Kiawah Island, Coastal Charleston’s Private Preppy Paradise

The South Carolina island, which has hosted guests like George Clooney and Donald Trump, boasts some of the best golfing in the world.

AUG 30, 2017

Off the mossy, oak-lined coast of Georgia and the Carolinas, there are several posh island retreats beloved by the Goyard-toting elite: Sea Island, St. Simons, Jekyll, Amelia, and Hilton Head, to name but a few.

And then there’s Kiawah Island.

Arguably the most luxurious and insider-y of the small islands dotting the coastal South, a number of billionaires, VIPs, and celebrities call Kiawah Island’s ten miles of beaches home. What separates it from the pack, however, is its highly private nature: Kiawah can only be fully enjoyed by property owners.

While there is a gorgeous five-star hotel called the Sanctuary allowing non-residents to at least get onto the island (and stay overnight), Kiawah deliberately goes out of its way to exclude everybody but residents who have club memberships, cocooning its secrets and restaurants and spas in ever smaller and more exclusive enclaves, like a series of Russian nesting dolls.

Without a full-service Kiawah Island Club membership (which runs more than $100,000), the island’s forbidden fruit is limited. No doubt you’ll have an amazing time, but you can’t access the bevy of amenities—the restaurants, golf courses and private special events—that are the main Kiawah draw.

Located 21 miles away from Charleston, the gated island’s various communities count 4,200 residents—and for most of those people, the houses are second, third, or even fourth residences. As is always the case, there’s a hierarchy, and pleasures don’t come cheap: one house is currently on the market for $22 million.

The crème de la crème of Kiawah’s gated communities is called Cassique, boasting coastal “cottages” and golf course views, and in closer proximity to Charleston than other areas of the sprawling island. Other communities, such as Marsh Island Woods and Oyster Rake, offer a more affordable slice of island life, with condos from half a million dollars.

“Kiawah is the perfect blend of southern beach vibe but with upscale resort amenities,” says Kim-Marie Evans of the site Luxury Travel Mom, who lives most of the year in Greenwich, Connecticut and has been coming to her home on Kiawah for 11 years with her four children in tow. “I love taking my kids paddle-boarding in the Kiawah river every morning. Dolphins literally swim up next to us, and no matter how many times it happens, I still scream with excitement. But when we are done, there is staff to put the board away and a cocktail waiting.”

Indeed, it’s that balance between leisure and luxury that makes Kiawah so special—and makes it a magnet for well-heeled homeowners over Easter, the Fourth of July, Thanksgiving, and Christmas. During the holidays, residents fly in on jets from New York, Connecticut, or Massachusetts, dress the kids in matching Lilly Pulitzer and Roberta Roller Rabbit outfits, and hire photographers to take Kennedy-style family shoots at one of the many picturesque Lowcountry spots throughout the island. Seemingly everybody on Kiawah has four children (four is the new three), and they are all impossibly, improbably well-behaved.

Perhaps it’s because the island’s delights are a kid’s—and adult’s—dream come true, tailor-made to relieve any stress (whether of the playroom or boardroom variety): 10 miles of master-planned beaches, two private golf courses, 30 miles of paved bike paths, horse trails, oysters roasts, dolphin pods, full-moon kayaking, and food trucks.

The island also boasts some of the world’s best golfing. Its seven golf courses were designed by household names like Jack Nicklaus, Gary Player, Tom Fazio, and Pete Dye, and include the elite Ocean Course, home to the 2012 and 2021 PGA Championship. The destination golf has reportedly roped in many a Kiawah faithful, although they come back for the extras like sake tasting classes, celebrity concerts featuring face-painting and food trucks, parent/child tennis tournaments, holiday extravaganzas, and a dreamy, Norman Rockwellian atmosphere that makes Mayberry look like New York City.

The neighbors aren’t bad, either; when I was recently on the island, those in residence included a popular congressman and a household name musician, while past guests have included such power players as Bill and Hillary Clinton, Joe Biden, George Clooney, Reese Witherspoon, George W. Bush, and even Donald Trump.

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For those hoping to snag a piece of the Kiawah lifestyle, there are two options: befriend somebody with a Kiawah home (and full club membership) and get them to invite you, or buy your own. While, yes, you can rent a home on VRBO, it’s the equivalent of staying at the  or : lovely but limited. It will be a relaxing vacation with scads of resort amenities … but one without the keys to the private kingdom.

Of course, Kiawah isn’t for everybody: there’s no real nightlife to speak of and only one small (albeit luxurious) shopping center. Of equal importance—the private nature of the island could make socializing difficult for the shy, not to mention for those who can’t make it down during the busy periods when the island comes alive.

For the indoctrinated like Evans, however, there’s no alternative.

“How can Kiawah be considered anything but heaven?”

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