Image: Kona Village Resort
Associated Press
While being the CEO of Apple can't leave much time for leisurely jaunts, Steve Jobs often whisks his family away from their home in California to the high-end Kona Village Resort in Kona, Hawaii.
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updated 9/17/2008 6:15:45 PM ET 2008-09-17T22:15:45

If you had all the luxuries money could buy, where would you choose to vacation?

To Botswana for a safari? To Antarctica for a cruise? Private palace in India?

It's not because they can't afford it, but for some reason many who landed on the Forbes 400 list of richest Americans stay closer to home than you might expect.

New York City mayor, Michael Bloomberg, for example, keeps a residence in Vail, Colo., to complement his home in Bermuda. When he heads to the islands, the billionaire politician might hang out with his neighbor — and another of America’s wealthiest men — Henry Ross Perot. While golf is the main activity in the opulent Tucker’s Town neighborhood that both men call their occasional homes, fishing and sailing are other favorite pastimes. But like most places where the Forbes 400 go to get away, it’s not necessarily the activities, but rather the privacy factor, that make Bermuda so popular.

“Aside from the obvious — breathtaking views, turquoise water, pink sand beaches— Tucker’s Town offers exclusivity,” says Kelly Petrone, public relations account supervisor for the Bermuda Board of Tourism. “Access to the primarily residential area is restricted. Residents and invited guests must first pass by a guard house. People who do not live in Tucker's Town are not generally allowed in the eastern part of the town, or onto the Tucker's Town Peninsula which extends along the southeastern edge of Castle Harbor. The town also previously included a private beach that has recently re-opened as Tucker's Point Club, an enclave of estate and town homes, custom homes and private residence club villas.”

When media mogul Rupert Murdoch seeks a sanctuary, he retreats to the family ranch in Carmel, a ritzy seaside town on California’s central coast where property comes at a pretty penny. The billionaire, an adoptive Californian, spends around three weeks a year relaxing in the valley and horseback riding on the sprawling estate. The remainder of his leisure time is spent sailing the world aboard his ocean yacht.

Like Murdoch, the majority of Forbes 400 elect for warm weather escapes. The Caribbean, in particular, has long been a favorite region for the wealthy because of its tropical atmosphere and proximity to the mainland. Brit billionaire Richard Branson's Necker Island in the British Virgin Islands sees more than its share of important people, Steven Spielberg and Oprah among them.

Other parts of the BVI — specifically, the unpretentious yet posh Bitter End Yacht Club — serve as a playground for billionaires of the sailing set. Pals Larry Ellison, the CEO of Oracle, and David Geffen, co-founder of Dreamworks, often travel there to play aboard their yacht, Rising Sun. John Glynn, vice president of North American sales for Bitter End, believes the BVI attract many of these wealthy sailors “because there are many ‘like-minded’ boaters” who frequent the area, as well, and “they like to blend into the fabric of a vibrant, casually elegant resort and boutique marina.”

Image: Tucker's Point Club
Associated Press
Ross Perot first purchased a plot of land in the gated enclave Tucker's Town in 1985, and since has acquired various pieces of adjacent property that now comfortably accommodate his wife, five children and a whole army of grandkids.
“This is all in addition to the natural beauty, idyllic harbors and great weather in the BVI, of course,” he adds. “The North Sound, where Bitter End is located, is perhaps the best deepwater anchorage in the Caribbean and among the best in the world. It’s not unusual to see 30 or so megayachts of more than 150 feet anchored out or on our docks on a winter evening.”

Another facet that might factor into them choosing the BVI is the chance to fly under the radar, something that’s more manageable at Bitter End than most star-heavy locales in the Caribbean.

“They all manage to maintain their anonymity while in the area,” Glynn reveals. “The paparazzi tend to stake out places like St. Barts, St. Tropez, and other high-profile destinations. The BVI are a little more low-key and don’t have the concentration of celebrity types — and far less hustle and bustle.”

Perhaps even more surprising is how undemanding these well-to-do guests often are. “It’s rare that we get asked to do outrageous things for overtly wealthy clients,” Glynn states. “Most things are fairly standard. This past May we hosted a 50th wedding renewal for a prominent family that included their yacht, a small cruise ship, rooms in the hotel and a major musical attraction. More typically, we would do an exquisite dinner on the beach for the yacht owner and his or her guests. But more often than not, one might just bump into these folks in our Clubhouse Restaurant, or in our pub, and not really know who they were.”

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