Lanai — Hawaii’s Most Exclusive Island Paradise

It’s been a Mormon colony, home to the world’s largest pineapple plantation and an elite playground for celebrities and the ultra-rich. But one thing Lanai has never been is a mass tourist destination. The sleepy island — Hawaii’s sixth largest — was never built up like its closest neighbor, Maui, which is just nine miles away. Perhaps that’s because Lanai has, since the 1870s, been privately owned; it wasn’t until 1990 that the first resort opened on the 140-square-mile island, built by Los Angeles financier and developer David Murdock.

Since then, Lanai has changed hands, from one billionaire to another — Murdock sold it to Oracle’s Larry Ellison in 2012 — but Ellison didn’t choose to go on a massive building spree. Instead, he set about transforming the island’s two existing Four Seasons properties — the Four Seasons Lanai and the still-yet-to-reopen Lodge at Koele — into resorts fit for, well, a billionaire.

When you arrive at the beachfront Four Seasons Lanai (, which opened last year after an eight-month, $75 million renovation, you definitely feel like you’ve scored an invitation to a very exclusive private club. (Cost of entry: $1,075 per night and up.) The open-air lobby is all warm wood and mod furniture mixed with traditional Hawaiian and Polynesian artifacts, like an enormous 19th-century Koa Hawaiian outrigger canoe that takes center stage.

To one side is the swanky Nobu, where you can feast on the signature miso cod sitting on the patio overlooking meandering grotto-style pools and beyond to the sparkling blue Pacific and rocky Hulopo'e Bay. (There is also a steakhouse, One Forty, and an outpost of L.A. favorite Malibu Farm.)

Wooden walkways wind through lush flowering gardens and past koi ponds to the 213 rooms and suites, all done in a neutral palette with parchment wall coverings, zebra-wood accents, hand-woven rugs and locally made artwork. The most luxurious of them is the two-bedroom Alii Royal Suite: For $21,000 a night you get custom-made furnishings, a double Japanese soaking tub and lots of bespoke touches, from handmade wallpaper to original, specially commissioned artwork. But it’s really all about the views — from nearly every room and terrace of the 4,000-square-foot suite, you’re never without an ocean vista. 

In the past, golfers would take the 45-minute ferry ride over from Maui to play the links at the Jack Nicklaus-designed cliffside Manele Golf Course, but now it’s only open only to guests of the Four Seasons. That means you don’t have to share those 18 holes — or the $6,500 Golf Boards (a kind of high-tech scooter that holds your clubs) — with the hoi polloi.

If you decide to explore the island beyond your idyllic little slice of beach, the resort can arrange for horseback rides around the base of Lanai’s highest peak, Lana’ihale, ATV rides in the rural countryside and boating around the island, where you’re guaranteed to spot dolphins galore — and maybe even a humpback whale or two. What you won’t see: hordes of tourists or tacky souvenir shops. You’re guaranteed an authentic Hawaiian experience, the way a billionaire would imagine it.

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