Billionaire Larry Ellison is reimagining the exotic island of Lanai€”but does this paradise need improving?

“You really should go see a movie” is an odd thing to say to someone on a tropical vacation, especially when that vacation is on Lanai. After all, this is the jewel in Hawaii’s crown, a tiny postage stamp of perfection with only 3,000 people that’s spread out over 365 idyllic square kilometres. So when a third resident echoes this to me while I am enjoying one of Lanai’s spectacular beaches solo (this is a private island), I have to wonder why on earth anyone in their right mind would choose a darkened movie theatre over the picturesque spoils of this land. “We’ve got the best movie theatre in all the state right here, man,” says the local. “State-of-the-art surround sound, reclining seats—and it’s cheap. All thanks to Uncle Larry.”

Uncle Larry is Larry Ellison, the billionaire founder of the software firm Oracle who, in 2012, famously purchased 98 percent of the island, with the stated goal of turning it into one of the most environmentally sensitive destinations in the world. I had been to Lanai before, several years ago, and even before Ellison purchased it, it was a legendary destination for Hawaii-goers. Oahu and Maui were the usual spring-break suspects for West Coast-ers, Kauai for the slightly more intrepid—but still also within the purview of said spring-breakers. Lanai’s cult status stemmed from the fact that it was almost impossible to stay here unless you could afford the Four Seasons. The island’s sole accommodation (save for 11 rooms at the quaint circa-1923 Hotel Lana’i) comprised the Four Seasons’ two sites—the oceanfront Manele Bay and the smaller Lodge at Koele—so if you weren’t comfortable forking over the equivalent of a down payment on a condo for a room, you were essentially shut out of the Lanai experience. But then Ellison stepped in—to make it more upscale. My initial thought (shared by more than a few, I imagine): who wants to improve perfection?

All by Myself

But nostalgia can be a funny thing, a sentiment I realize as soon as I step into the lobby of the redone Manele Bay. My first impression, despite my previous visit, is that I’m in a hotel I’ve never been to before—the drive from the marina seemed familiar enough, and I definitely recall pulling into a long winding driveway, but in my memory the hotel was a formal affair, ample marble punctuated by garish swaths of aqua and pink, as if A Flock of Seagulls had a hand in the design. But standing in a large open-air lobby that’s equal parts dark wood and unencumbered vistas, I feel like we’re way past “a new coat of paint and new mattresses” territory. It’s only as I make my way to my room and glimpse a view of Hulopoe Beach that I begin to reorient myself. The old hotel always felt as if it were taller than its four storeys, whereas now, even as I glide down a flight of stairs, the new place feels like I’m in the world’s largest Frank Lloyd Wright Prairie-style bungalow.

I drop my stuff into a ridiculously large room (and this time it isn’t just in my mind, as I later find out: the number of rooms has actually decreased and the ones that are left are noticeably bigger), and as I plan my next steps I have a welcome sense of déjà vu. Planning your day at Lanai has little in common with a stay at any other island on Hawaii, where even the most luxe properties require you to schedule things like golfing or car rentals. Here, I pick up the phone and say I’d like to go golfing, and voilà, I’m in a buggy heading to the pro shop, and it turns out I have the course to myself. I ask the pro if it’s all right if I start on the ocean-hugging back nine, and while his mouth says a very polite “Of course, sir,” his eyes give me a look that says, “Dude, you can play in your underwear using a hockey stick for a club, for all I care—you’re the only one here.” Thankfully, my greatest fear—that I’ll shoot the round of my life and no one will witness it—is avoided, though hacking the ball all over hell and creation does give me insight into another aspect of the average Lanai golfer—unlike me, they don’t search for balls they’ve hit out of bounds. By the end of nine holes, I’ve found so many balls that I’m of half a mind to set up a links-side sales stand—until I remember that, for today at least, I’m the only customer here.

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After my round, I make the easy stroll down to the beach, and as I nod at whom I pass, I marvel at the irony that the higher up the food chain you go, the more relaxed things become. I’m a collegial enough sort, but I’ve never exchanged pleasantries with strangers anywhere else in Hawaii, like Waikiki, partly because that’s a lot of hellos, but more so because it’s simply not done. Here on Lanai, the isolation brings a sort of band of brothers repartee, if only because it quickly becomes clear you’ll be running into the same cast of characters throughout your stay, so you might as well be friendly. The beach at Manele is not dissimilar to many other Hawaiian beaches—it’s much better than most for snorkelling, much worse for surfing—but the key is that you have it to yourself. You find a patch of sand you like, you attempt to throw down your towel, and an ever-present staff member bolts across the sand to try to do it for you. If you want to snorkel, you go to the shack and they set you up: no resort fee, no egregious rental fee, just a “here you go, have fun” as if you were staying at a wealthy uncle’s house. If your uncle were Uncle Larry.

But trying to get a glimpse of what Uncle Larry has done to the island from the perch of a deck chair with a chilled skewer of pineapple is hardly Woodward and Bernstein territory, so the next morning I rent a Jeep and head into Lanai City. Driving on Lanai is a bit of a mind trip—there are no stoplights and, thanks to Ellison’s infrastructure spending, the roads are pristine and rarely used—though the police (all recent graduates from the Maui Academy) are relentless with speeding tickets nonetheless. Legend holds that one unfortunate flatfoot snared a certain David Ellison (son of Uncle Larry) in such a trap, proceeded with the ticket and quickly found himself transferred off the island. My trip holds no such surprises, though as I near town I do spot several fading NO WINDMILLS ON LANAI signs but once in town all anyone wants to talk about is the movie theatre. The town itself is the most charming example of a company town you’re likely to find. Built by the Dole Corporation in the 1920s, it is arranged around a huge park, like a mini-Manhattan but with Norfolk pines and hardly any people. But other than the movie theatre, it’s exactly as I remember it—especially the famed Blue Ginger restaurant, where an egg salad sandwich is still $4 and locals and the occasional Four Seasons refugee mingle on a series of salvaged chairs.

Lost Coastlines

After lunch I head off the paved roads—there are over 400 miles of unpaved road on the island and about the same number of cars that you’d find in the average Safeway parking lot—and it’s only then I remember the one thing that no other place can match Lanai for: unspoiled space. Miles and miles of it, just as on my last visit. I drive by the former Lodge at Koele, eerie in its quietness—it’s still under renovation, with no particular end in sight—and continue down to Shipwreck Beach, where I brave whipping trade winds to catch a glimpse of the WWII-era container ship, wrecked and rusting on a reef just offshore, even more eerie in its quietness. But for the most part, I just tool around with no plan, because I don’t need one.

I reward myself for a very lacklustre day of sleuthing with dinner at Nobu Lanai: two words that seem about as compatible as “President Trump.” Weirdly, here I do need a reservation, but as I pop in, it seems that courtesy is mostly for the sake of the kitchen, as the starkly beautiful room is far from full. Nobu is one of Lanai’s flashier new additions, and the level of precision paired with the freshness of the sushi evokes a brief hit of envy over how this island, with its abundant physical gifts, also gets to have a restaurant this good. But there are worse things than having to put up with an embarrassment of riches.

In the past, once you’d rented a Jeep and seen the town, you’d essentially exhausted all the non-beach and -golf activities on Lanai, but one gets the impression that the peripatetic Ellison, who, in addition to being the founder of Oracle, also flies fighter jets and runs the champion America’s Cup crew, wanted more things to do for his guests. I go trap shooting at a new course that is the Nobu of sporting clays, but I just as easily could have gone horseback riding or visited a flight training centre, where I’m told I could “learn to perform basic flight manoeuvres, such as takeoff, cruising and landing.” When you have the ability to pay $550,000,000 for an island, I think your understanding of the word “basic” is slightly elevated, but I’m tickled that becoming a pilot is an option.

I never do see a movie—Tom Hanks in Inferno is showing—because in what seems like a blink I’m back on a ferry headed to Maui. Soon I’ll be dealing with stoplights, lineups and reservations, and the option of flying an airplane will cease to be a reality. But I know that a place that has all those things exists, and while I can’t say whether the presence of Uncle Larry is good for Lanai, I can attest that I’m willing to drop anything, any day of the year, to go back and keep trying to find out.

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