Hawaii island, superyachts and fighter jets: Lavish retreats of Larry Ellison, briefly the world’s richest man ahead of Elon Musk

Ellison, 81, owns more than 40% of Oracle, the Texas, U.S.-based software giant that constitutes the bulk of his wealth. His net worth jumped by $89 billion after Oracle’s quarterly results surpassed analysts’ expectations and projected more growth. The surge lifted his fortune to $383.2 billion on Sept. 10, placing him ahead of Tesla CEO Elon Musk for much of the day before Musk edged back by $1 billion, according to Bloomberg.

Sensei Lānaʻi resort on Lanai island. Photo courtesy of Four Seasons Resort Lānaʻi 's Instagram

Ellison’s childhood love for Hawaii culminated in his $300 million purchase in 2012 of 98% of Lanai island, where Bill and Melinda French Gates were married, according to CNN. On Lanai, Ellison partnered with physician David Agus, who treated his late friend Steve Jobs, to launch Sensei, a chain of luxury wellness resorts focused on longevity.

According to Australian newspaper The Sydney Morning Herald, his personal connections have drawn high-profile visitors such as Musk, actor Tom Cruise and Israeli Prime Minister Benjamin Netanyahu to the island.

He has also implemented renewable energy, sustainable agriculture and conservation projects with the goal of turning it into a model of sustainable living that could be replicated globally. Though he now lives full-time in Hawaii, Ellison’s real estate portfolio across the U.S. is valued at about $1.75 billion, according to lifestyle magazine Robb Report.

His most famous mainland residence is a 23-acre estate in Woodside, California, modeled on 16th-century Japanese feudal architecture, according to Pressfarm, a PR and media outreach platform. The property, estimated to have cost over $200 million, features Japanese gardens, koi ponds and a man-made lake that used materials such as wood, tiles and stone lanterns imported directly from Japan.

Ellison also owns 12 properties on Carbon Beach in Malibu, California, often called "Billionaire’s Beach," and an estate on Lake Tahoe where he enjoys privacy and sweeping mountain and lake views.

The $200 million Rising Sun yacht once owned Larry Ellison. Photo from Instagram

For Ellison, the ocean is a second home. He began sailing as a young man and pursued competitive racing in the 1990s after acquiring a 78-foot yacht named Sayonara, Business Insider reported.

He has since spent hundreds of millions on the sport, won a second America’s Cup in 2013, and launched SailGP, a global catamaran racing league backed by celebrity investors.

Ellison once owned Rising Sun, a 453-foot megayacht that reportedly cost more than $200 million to build, before selling it to media mogul David Geffen. In 2010 he downsized to Musashi, a 288-foot yacht named after Japanese samurai Miyamoto Musashi, built in minimalist style and costing about $160 million.

According to lifestyle magazine Luxury Launches, it features a basketball court with a powerboat trailing behind to retrieve stray balls from the ocean, as the Oracle founder does not like to pollute. "He has a lot of toys, at the highest level," journalist Julian Guthrie, who interviewed him for her book "The Billionaire and the Mechanic," told the New York Post. "He gets a lot of pleasure out of beautifully designed [things]."

Another prized vessel is Katana, a 244-foot yacht built by German shipyard Blohm + Voss, known for its sleek design, private cinema, gym, and luxury cabins.

World's second richest man and founder of Oracle, Larry Ellison. Photo from Instagram

For a man who values time and privacy, private jets are indispensable. Ellison owns several, including a Gulfstream G650, one of the fastest and most luxurious business jets. His customized Gulfstream once made Steve Jobs so envious that the Apple co-founder ordered the same model, Luxury Launches reported.

In the late 1990s, Ellison often flew an SIAI-Marchetti S.211 fighter trainer, once used by the Italian Air Force, and staged mock dogfights over the Pacific with his son David. He also tried to import a decommissioned Russian MiG-29 fighter jet, but U.S. authorities initially blocked the move.

"It’s considered a firearm, even though that’s not my intention," he told British newspaper The Guardian in a 2000 interview. It is disarmed, but theoretically you could rearm it and take out a couple of cities."

Some reports suggest the jet eventually entered his collection.