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Lanai: The island less traveled

Exploring the new Lanai

Scuba diving in the underground cathedrals of Hulopoe Bay.

It’s a rough life for a visitor in Lanai: I wake up in a spacious and impeccably designed room offering ingenious high-tech touches, including a TV beautifully embedded in the bathroom mirror and a toilet lid that lifts as I enter. 

Before getting out of bed, I push a button to open the shades and am greeted by a gorgeous view of the lapping waves of Hulopoe Bay from my bed at Four Seasons Resort Lanai.  

With the touch of the resort-supplied iPad, I’ve ordered a plate teeming with mango, kiwi and other tropical fruits to eat on the lanai. Two free-form pools below beckon.  An in-room massage, a beach-side yoga class and a mountain bike ride tempt.

On this day I take an expedition to explore the storied past of this corner of paradise. During the drive with preservation expert Kepa Maly I grasp what extraordinary things are happening on Lanai.

As recently as last decade, the outlook was dismal. In 2009, Lanai City was named one of America’s 11 Most Endangered Historic Places by the National Trust for Historic Preservation. Remains of Dole’s enormous pineapple plantation, built in the early 1900s, were left behind to scar the landscape. An earlier incarnation of the Four Seasons lacked ambiance and profitability, not just a tourist issue but an employment concern for the 3,000-plus locals. 

Today’s Lanai, the island less traveled, finds itself in the midst of a rebirth, thanks to its owner, Oracle co-founder Larry Ellison. 

Yes, that’s right; Ellison bought almost every one of the 140 square miles of the Hawaiian island. His vision balances a respect for its past with an eye on a sustainable future. That’s good news for island worshipers seeking a travel experience that blends authenticity with extreme comfort. 

Here’s why Lanai is having a moment: 

Larry Ellison, savior. In 2012, the tech entrepreneur and philanthropist bought all but 3 percent of Lanai. “It’s amazing,” Mike, a skeet shooting guide, marvels. “How do you own a Hawaiian island?” 

The easy part when you’re a billionaire: Drop hundreds of millions of dollars to buy the land. The impressive follow-up: Keep spending to revive what remains of a forsaken pineapple plantation and the ill-conceived efforts of a previous landlord to commercialize the island. 

Natives first. Before turning his attention to tourism, Ellison (who reportedly owns several homes on Lanai) focused early on the residents, most of whom live in classic plantation cottages in Lanai City. Homes were painted and businesses spiffed up. The long-closed community pool was rebuilt.

Now the humble town square has come to life with a revamped park, funky shops, simple restaurants and a newly opened state-of-the-art movie house. This Ellison-fueled progress has secured jobs for many. 

Reinventing a resort. Accommodation options are limited in Lanai and range from low key to luxury. Lanai City, which sits 10 miles from the beach, offers the historic 11-room Hotel Lanai and several Airbnbs. 

Charming as those may be, you go to Lanai to stay on the beach. And that means booking Four Seasons Resort Lanai, where nightly rates range from $1,150 to $21,000 for the three-bedroom Alii Royal Suite. 

Under Ellison’s stewardship, the resort reopened this year after a multimillion-dollar transformation, featuring 213 guest rooms and suites, an ocean-view fitness room and a new spa. (Take note massage fans: I recommend the flowing Hawanawana massage.) 

Out went a turquoise swimming pool with concrete edging the remains of a centuries-old Hawaiian village. In came new landscaping and waterways around flowing pools built to enhance the natural lava rock landscape and embrace the heritage ruins.  

With plenty of padded beach chairs to choose from, I don’t have to worry about getting up early to reserve a spot as I do at other beach resorts. The grotto-like setting feels secluded, yet never far from attendants who clean sunglasses, offer complimentary sunscreen and set you up with a cooler of icy water.

Though I’m not a golfer, I can’t help but admire the resort’s Jack Nicklaus-designed golf course, where every hole has an ocean view. (The 12th green is so spectacular that Bill and Melinda Gates were married on it.)

Eating well. The Four Seasons’ dining choices are more varied than you might expect at an isolated resort. Like the lobby and most public spaces, they are open-air to embrace the soft island breeze. 

The Lanai outpost of Nobu offers local seafood and sushi or a fun teppanyaki experience, the fresh vegetables and fish carefully prepared tableside. The main dining room, One Forty, featuring American and Hawaiian food, is playfully named for the temperature for grilling steak as well as the size of Lanai. The resort’s sports bar offers a chance to stay connected to civilization, or at least a favorite sports team, with its 90-inch TV. Other dining options: the poolside Malibu Farm and the golf course’s lunch spot Views.

With such choices, it’s tempting to stick close to the Four Seasons, but visitors coming for more than a couple of days might consider taking the resort shuttle into the sweet town. I had a tasty poke and rice lunch ordered from the counter of the town’s only market. Mike also recommends Lana’i Ohana Poke Market (get there before food runs out) and Blue Ginger Cafe, known for its turnovers and a serving of the latest island gossip.

By the sea. A white sand beach edges Hulopoe Bay, a short stroll from the resort. The Four Seasons’ share of the cove offers lounge chairs, umbrellas and snorkel gear – even prescription masks. Though humpback whale or spinner dolphin sightings are common, all I spot are three outrigger crews practicing along the coast.

Slightly further east sits Manele Harbor, a place to catch a ferry for a day trip to Maui, take a scuba journey or charter a yacht. That’s where I board a catamaran for an afternoon of snorkeling at Shark Fin Cove (no worries, the only “shark fin” is a rock formation). On board I eat a picnic lunch at the foot of towering and breathtaking cliffs where King Kamehameha once had his summer fishing retreat. 

Going up-country. The Four Seasons footprint reaches to the center of the island, where its inland property, the Lodge at Koele, is undergoing its own transformation for a more landlubber experience. Even while construction continues, visitors can explore island trails by horseback or hone skeet shooting or archery skills. I surprise myself by successfully shooting several clay pigeons and failing miserably at hitting the archery targets.

Appreciating Lanai. Four Seasons was rebuilt to embrace the island history with its pleasant décor of beautiful crafts and artwork and museum-quality displays in the main lobby, including the centerpiece, a lovely, 100-plus-year-old Polynesian canoe. 

There’s more to learn about the history in town at the Lanai Culture & Heritage Center, a museum overseen by our expedition guide, Kepa Maly. 

On our excursion, he drives to an ancient ceremonial site, recently restored under Ellison’s corporation. Maly points to areas of habitat reclamation on an island where most of the vegetation was brought in by others, beginning in the 1700s with Captain James Cook. 

The work is just beginning, Maly says. “It’s a new era.” 


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