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Billionaire Island: Why Lanai Should Be Your Next Vacation Spot

photography courtesy of FOUR SEASON RESORT LĀNA’I

Lanai vacation
Formerly known as the pineapple island, today chic luxury is at the heart of this private and pristine Hawaiian Island.

In Lāna’i, it’s normal to go on a four-hour hike and not run into a single person. When you’re on the smallest of Hawaii’s islands that is home to only 3,200 residents; when you’re vacationing in a place that clings tightly to its virtually untouched, pristine culture and way of life, you will understand why Lāna’i fights to stay this way.

The exclusivity and VIP vibe of this island is unlike any of the other Hawaiian Islands. Far from crowded beaches littered with people, Lāna’i is completely unspoiled. Though very different from what most people envision when they imagine a Hawaiian vacation, the mystery behind Lāna’i creates quite an allure for this off-the-beaten-path island.

Lanai vacation beach

Here, we uncover some of the mysteries of Lāna’i, how it came to be called Billionaire Island, and why you need to pay this place a visit.

Let’s start with the fact that 98 percent of this island is privately owned by billionaire Larry Ellison, founder of Oracle. Ellison purchased it back in 2012 from David Murdock who gained it from James Dole as part of Murdock’s purchase of the Castle & Cooke company.

But the history of Lāna’i dates back much further than that. Let’s rewind time to the 1500s to understand this mystical island. As the story goes, the son of Maui’s chief caused so much chaos when he destroyed a crop of breadfruit trees that, as a form of punishment, he was banished to the then-uninhabited island of Lāna’i, known to the Maui people as the “island of spirits.”

Legend has it the chief’s son rid the island of its evil spirits while there, and named the island Lāna’i, meaning “Day of Conquest.” People migrated to Lāna’i from Maui, and thus began its life as a settled island.

Lanai sunset

Jump forward more than 400 years when the first known wealthy owner joined the scene of Lāna’i. James Dole of Dole Pineapple purchased the island for $1.1 million in 1922. He had great hopes for Lāna’i and established the majority of the island as we see it today. Dole grew Lāna’i into the biggest pineapple producer in the entire world, and it remained such until the production of pineapples overseas drove prices down, leaving Lāna’i in the dust. In 1992, the island said farewell to its pineapple production with its final pineapple crop harvest. The owner of the island at this time, David Murdock, switched gears and decided to develop Lāna’i as a tourism hotspot.

After pouring $30 million a year for numerous years into the island without seeing much return, Murdock put the island up for sale. The highest bid landed Larry Ellison as the current owner.

In 1992, the island said farewell to its pineapple production with its final pineapple crop harvest.

Lanai vacation resport

Tourism was the focus for Ellison with his purchase, and it still remains such today. However, Ellison’s vision of Lāna’i as a vacation spot was different than any other part of Hawaii. Ellison wanted to create a VIP experience for travelers that would make the island feel almost like their own private island—a place where they would be treated like royalty.

And that is exactly what he did. Four Seasons Resort Lāna’i is Ellison’s dreams actualized. With a penthouse suite that dons the price tag of $21,000 night, Ellison’s resort has won the title of the most expensive hotel suite in Hawaii.

However, that’s not the only award it has won. Four Seasons Resort Lāna’i proudly boasts a long list of accolades including U.S. News & World Report’s #1 Best Hotel in the U.S. for 2018 and Conde Nast Traveler Gold List status for 2018. But Lāna’i is for a different type of traveler; one who doesn’t mind a quiet and super zen approach to vacation.

Four Seasons Resort Lāna’i proudly boasts a long list of accolades including U.S. News & World Report’s #1 Best Hotel in the U.S. for 2018 and Conde Nast Traveler Gold List status for 2018.

Four Seasons Resort Lāna’i

Oozing with classic luxury and design, Four Seasons Resort Lāna’i is the ideal chic respite from your hectic life. Simply walking through the wide-open, airy entrance will release any stress you brought with you.

From there, you will be whisked away to your room which takes you on a stroll through the property’s jungle-like, lush greenery and wildlife chirping with joy.

Four Seasons Resort Lāna’i pool

By day, the pools are a great place to settle in and call home. Lagoon-style pools with waterfalls and jacuzzis create an idealic setting to spend your day. Don’t miss the adults-only area for an even more secluded retreat that will provide all the relaxation you could possibly imagine.

Don’t oversee the fact that there is a great beach right in front of you, Hulopo’e Bay, where epic snorkeling awaits. Either grab complimentary snorkeling gear from the resort’s beach kiosk and explore the waters on your own, or sign up for a luxurious snorkel sail at the resort’s activities desk for a beautifully guided tour to super-private snorkeling spots.

Manele Golf Course

One of the biggest draws of the resort lies in its Manele Golf Course. Whether golf is your game or not, you will appreciate the breathtaking beauty of this course. Jack Nicklaus designed Manele so that every single hole has ocean views. On some, you find yourself staring right over the edge of stunning cliffs that drop down to lava rocks and crashing waves below.

Bill Gates himself was so impressed with this course that he chose to make it his wedding spot. On the course’s signature hole, #12, Bill and Melinda Gates were married.


As the owner of Malibu’s NOBU restaurant, Ellison was able to bring the restaurant to the resort as well. NOBU LANAI is a dining experience unlike any you’ve ever had. Here you can sit in privacy, eating Chef Matsuhisha’s top-rated sushi and Japanese dishes with the ocean right in front of you and the brightest glistening stars above. And the best part? You won’t feel the rush of other NOBU restaurants as the seclusion and exclusivity of this location in Lāna’i allows you to soak up every moment of your epic meal.

Seasons Resort Lāna’I provides luxury from start to finish, including full service at the airport like greetings on the tarmac, refueling and catering.

Regardless of what way you prefer to do your vacation, here on Billionaire Island, your experience will never be anything less than sheer luxury.


Ready to enjoy luxe, iconic travel? Our exclusive luxury travel concierge is ready to create a fabulous trip for you. ICONIC LIFE has a joint collaboration with Concierge Extraordinaire, a premiere global travel consultant who provides extraordinary service our valued readers. Concierge Extraordinaire is a premier firm with a comprehensive portfolio of luxury, private and corporate travel experiences. This professional team offers lifestyle ambassadors who cater to distinguished clients. The firm’s global travel resources put the world of opportunity at your fingertips. Click here to connect directly to our global travel expert or visit Concierge Extraordinaire.

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