Top Vacation Destinations for Software CEOs

Like all of us, even the most high-profile CEOs need time to reboot. Among software leaders who choose to take time off from running their companies, Hawaii and California are the most popular, while Mexico and France deserve an honorable mention. Many CEOs prefer to stay off the grid altogether and sail on the high seas.

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Legendary software executive Marc Benoiff, the founder and CEO of not only sports Hawaiian shirts to work, but he also named his dog “Koa” after a type of tree native to Hawaii. Not to mention, the tech executive owns a 5-acre estate on the Big Island, which he bought for $12.5 million in 2000. Benoiff’s former mentor Larry Ellison, the CEO of Oracle, purchased the Hawaiian island of Lanai, including its two Four Season Resorts, for $300 million in 2012. Microsoft billionaire Paul Allen also owns a beachfront Hawaiian estate, while Michael Dell heads to his “Raptor Residence” retreat rumored to be worth $64 million.


Software CEOs don’t get much time to vacation, so it makes sense that one of the top places they go to squeeze in some R&R is in California, just close enough to Silicon Valley. Bill Gates is one of many who have shelled out for a property in the Golden State, buying an $18 million horse farm in Rancho Santa Fe which includes a racetrack, guesthouse, office, veterinarian’s suite, orchard and five barns. Oracle’s Ellison owns a private golf club in Rancho Mirage, and a beachfront home in Malibu. Scott Salkin, the founder and CEO of Allbound, likes to stay in the Bay Area, enjoying the tranquility of the bay, while Sausalito and wine country are just a drive away.