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The Island of Lanai: Heaven While Still on Earth

Spending my formative years in Hawaii and well-traveled throughout the islands of the South Pacific, I am no stranger to exquisite beaches with majestic swaying palms, crystal clear bathtub-warm waters, excellent hotels that enhance their island’s edenic blessings and the importance of engaging in cultural preservation in a rapidly changing and interconnected world.

In Hawaii’s island of Lanai – comma shaped and only 140 miles in radius – Mother Nature may have provided the ultimate natural canvas on which to paint an illustrious vision. So when Forbes-listed seventh richest person – Oracle Corporation founder Larry Ellison – with an estimated net worth of about $61 billion – took that canvas and with his recently acquired and renovated Four Seasons Lanai painted a masterpiece unveiling the ultimate dream-like resort, perhaps no one, not even Father Time, should have been too surprised.

The Pineapple Isle

For most of the past hundred years, Lanai was the world’s largest supplier of pineapple, hence its moniker the “Pineapple Isle.” In 2012 Ellison bought 98-percent of Lanai from Castle & Cooke’s David Murdock for a reported $300 million. That purchase included two hotels, the Four Seasons Lanai and the Lodge at Koele. The Four Seasons Lanai reopened in February 2016 following extensive renovations. The nearby Lodge at Koele is currently undergoing a $75 million redesign and is scheduled to reopen late next year.

In four blissful, yet action-packed days I spent on Lanai, one thing became as clear as Lanai’s crystalline Pacific waters. “Uncle Larry” as he’s affectionately known, has been great for Lanai, its 3,000 residents and Lanai’s once ailing economy. Optimism is the prevailing mindset. And one of Ellison’s future plans involves greenhouse-based, computer driven hydroponic cultivation to fuel the island community’s sustainability. While it’s easy to think of this experiment as the coupling of altruism and brilliant business acumen, it’s really something as simple as a wonderful way of thinking and makes visitors to this special island believe they are part of a greater good. What more could one possibly want from an island get-a-way?

The bed

At Lanai airport guests are greeted by hotel ambassadors and driven 20-minutes in comfortable Mercedes Sprinter vehicles. If arriving via Honolulu, check-in can be completed at the private Four Seasons airport lounge near gate 24. In fact, until check out – that took all of two minutes – I never had any occasion to visit the hotel front desk during my stay.

Arriving at the hotel, with just 213 rooms and suites, another ambassador gave me a brief property tour, handed me my “key” resembling a comfortable and convenient black fit-bit bracelet, then showed me to my room where my luggage was waiting. And what a room it was. An enormous space, nearly 700 square feet of Zen-inspired natural woods, two desks, sitting area, a 70-inch flat screen television, and famed Four Seasons bedding designed for sweet dream enticement. The balcony was larger than my first east coast apartment and furnished with enveloping chairs to bask in the expansive ocean view. Rooms were equipped with wondrous electronic touch switches for lighting and shades and the bathroom was fit for royalty containing Hawaiian A’ina products.

Also in the room a Nespresso machine, teapot and an I-pad containing island information and daily calendar of complimentary activities, such as yoga, Tai Chi, meditation, circuit training and “butts and guts” classes. For those desiring something a bit stronger, also on tap a mixology class to create delightful, delectable libations. There are also complimentary Hawaiian cultural classes and resident aviarist Bruno can teach you everything you ever wanted to know about Amazonian parrots – there are several gorgeous rescue birds on site – and he’ll probably get you to kiss Lulu, a gentle green yellow-necked parrot.

The activities

“Most guests stay four to seven days” David Arraya, the hotel’s Food & Beverage Manager said “since true disengagement doesn’t usually begin until day three.” While I am usually able to disconnect at Olympic speed, there are so many activities to try at, or very close to the hotel, I only scratched the offering’s surface. I could easily imagine staying a week.

As a tennis aficionado, I signed up for a private lesson with resident tennis pro Ryan Winters. With an easygoing manner, 1000-watt smile and skills made more impressionable since Ryan’s ambidextrous, he cajoled me with drills so I would best focus on court awareness. This was my first time playing on a Har-Tru court, a green clay with a silica top surface slightly different than traditional red. I’m not sure if it improved my game, but it certainly was a pleasure. At the end of the hour, sliced oranges, chilled towels and ice water appeared. While we rehashed the lesson, attendants re-raked the clay court, so it would be perfect for the next session.

At the main pool, adult pool and Jacuzzis overlooking the Pacific, pool attendants are just that: attendant, but not overbearing. They routinely brought by little pleasures like mini iced mochas, passion fruit milkshakes, skewered frozen fruit, and Evian spritzes to cool off. My personal favorite was the attendant who came by daily to clean sunglasses.

The newly completed state-of-the-art gym at the Fours Seasons Lanai may take the award for the most compelling view ever. As one runs on treadmills – in perhaps futile attempts to sweat off some of Chef de Cuisine Kemar Durfield’s exquisite desserts – floor to ceiling windows provide head on Pacific views giving blissful sensations of oceanic suspension.

Attempting to channel my inner Jack Palance, I went horseback riding. Located a short 15-minute drive away with plenty of wild turkeys en route, the stables are at 2,000 feet elevation and adjacent to Koele Lodge. Shortly before my visit, the hotel acquired a dozen adorable miniature horses and four miniature donkeys, a few nearly the same size as my Labrador. A veritable picture of cuteness, these Lilliputian beauties were surprisingly affectionate.

Climbing atop my handsome ride “Red,” rancher Si Jarboe, another couple and I rode through lava and ash amid towering iron wood trees. Stopping a few times for panoramic photos of neighboring Maui nine miles away, we turned a corner when I got a whiff of hanging guavas just off the trail. Si indulged me pulling down a branch, and I grabbed a few, biting into the tart, sweet taste that brought back memories of childhood.

At the Hawanawana Spa, I had perhaps the finest sports massage I’ve ever encountered. My masseuse Kino had the gentle temperament of a saint, a soothing voice and possessed hands like a satin-draped steel vice grip. Leaving I felt an inch taller, and so tension free and relaxed that when I went to sign the bill, I had to think twice about my name.

A close friend took the 40-minute ferry ride over from Maui and we hopped into a 4x4 jeep and drove into Lanai City. A lovely spot to stroll with a small park named after James Dole, a handful of quaint shops, two lunch cafes and a two-screen movie theater, but happily the name “city” is a misnomer. Make sure and stop in at the small, but well-curated Culture & Heritage Center reflecting the island’s pineapple past. At Michael Carroll Gallery talented local artists display their work.

Continuing north another 30 minutes first on pavement and then east on dirt, we made it to Kaiolohia, known as Shipwreck Beach. Rough seas, coral reefs and a rocky channel endowed the name, and many ships have been doomed there. The massive Liberty, a 1940’s tanker seen off shore however, was intentionally retired here as its final resting place.

Hulopo’e Bay, directly in front of the hotel is a protected conservation area, with excellent snorkeling just feet from the shore. Often spinner dolphins show up and delight with their antics. Nearby is Pu’upehe – Sweetheart Rock ­– where legend has it a young Maui princess drowned in high surf and her Lanai suitor was so distraught, he jumped from the 80-foot rock to his demise.

The meals

Dining at the Four Seasons Lanai is nearly a religious experience, and nowhere is this truer than at Nobu Lanai set overlooking Hulopo’e Bay.

Starting with perfectly grilled, slightly crunchy Shishito peppers, I continued with Bigeye tuna sashimi salad with tangy Matsuhisa dressing. The sushi and sashimi plate I next enjoyed contained delicacies so fresh – flown in daily from Japan or caught locally – they surely were swimming just hours earlier. The piece de resistance was the Kiawe wood smoked Wagyu beef gyoza blissfully married to Ms. Ginger Onion Marinade. The lilikoi coconut mango cream mousse dessert was light as a cloud following a spring rain and had a touch of zest making me think of a summer kiss.

The plein air Sports Bar quenches more than thirst. An excellent fresh mint Mojito followed by a savory grilled Kalbi plate with house-made kimchi was scrumptious. Though there are big screen televisions discreetly tucked in the corner and pool tables, this is no ordinary sports bar. It faces the ocean and has a complete menu with items like venison pizza and Wagyu skirt steak. Leave room for the divine s’mores cheesecake.

At Restaurant One Forty mimicking the island’s radius and perfect temperature for a medium steak, I obliged and had a Wagyu New York cut so flavorful and so tender, my knife was bored.

For lunch poolside, Malibu Farm – of L.A.’s Malibu Beach fame – prepares a delicious chopped salad using local and organic ingredients.

Breakfasts were also inspiring. Favorites were a grilled Ahi Benedict with “lava” sauce: hollandaise with Sambal, plantains, tomato and passion fruit, and a tofu scramble so delicious it completely defied its healthy connotations.

The lesson learned

There are many beautiful islands in the world and many world-class hotels and restaurants. However, in equal parts because of Lanai’s beauty, the kind, generous spirit of its residents, and Larry Ellison’s unique vision, a Four Seasons Lanai experience will be relaxing, rejuvenating, and utterly unforgettable. By the time you leave, you’ll already be plotting your return to Hawaii’s Pineapple Isle.

Julie L. Kessler is a travel writer, legal columnist and attorney based in Los Angeles and author of the award-winning book “Fifty-Fifty: The Clarity of Hindsight. She can be reached at

Julie L. Kessler

Written by Julie L. Kessler

Julie L. Kessler is Money Inc's Senior Travel & Luxury Editor and writes for several major media outlets in the U.S. and overseas. She is also an attorney and legal columnist and the author of the award-winning book "Fifty-Fifty: The Clarity of Hindsight." She can be reached at

Read more posts by Julie L. Kessler

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