Billionaire Oracle head Larry Ellison parks his $200 million yacht, the Rising Sun, at the Yacht Haven Grande marina in Charlotte Amalie, St. Thomas. The luxury marina is the only one in the Caribbean that can handle the mega-yachts. “Historically, marinas have been about parking and storage, but with the development of larger and larger boats, the focus has shifted to one of service,” says Chuck Smith, the property’s PR director.

Microsoft co-founder Paul Allen likes to park his 416-foot yacht, Octopus, in St. Barthélemy in the French West Indies. It’s the ideal spot for Allen and his ship, which contains a 10-person submarine and two helicopters. The turquoise water, white sand beaches, and shops like Cartier and Hermès beckon on this French isle, a parcel of paradise by almost anyone’s definition. The lone airport is basically a seaside landing strip that can only handle small aircraft; that and an absence of very large hotels keeps the crowds away from St. Barts, amplifying its hideaway stature.

Since 1999, Google founders Sergey Brin and Larry Page have been attending Burning Man festival, the counterculture extravaganza honoring "radical" self-expression. A mecca for unique art installations, past pieces have included an enormous burning bra, robotic spiders, and a 12-foot-tall mosaic vase with stainless steel daisies. To pay tribute to the weeklong event, during its occurrence, Brin and Page have placed the Burning Man icon on the second "O" of their Google home page. "Burners" must bring all their supplies including water and food as nothing except ice and coffee is sold in Black Rock City, the elaborate temporary community constructed for festival.

In 2004, Revlon mogul Ron Perelman sold his oceanfront Palm Beach estate, Casa Apava, for a record $70 million, but he’s held on to his 57-acre compound called The Creeks in East Hampton, Long Island. Set on scenic Georgica Pond, the estate has a 100-seat screening room, guest quarters separate from the main house, a private security staff and celebrity neighbors like Steven Spielberg. This past August, Perelman hosted a fundraising event for Hillary Clinton at his pad. The seated dinner went for a cool $4,000 a plate, while cocktails by the pond commanded $1,000.

Windswept and history-rich, the onetime whaling capital of the world offers the sensation of splendid isolation to those who can afford it. That would include Fidelity’s Abigail Johnson, who owns a beachfront home on the island. Tommy Hilfiger, Tim Russert, Jack Welch, Jerry Stiller and Anne Meara, have residences there too. Most of these are outside Nantucket Town, whose cobblestone streets lined with gray-shingle buildings are packed with tourists in summer but take on a haunted quality at other times of the year.

Public Storage founder B. Wayne Hughes’s Spendthrift Farm is located in the heart of Kentucky’s verdant thoroughbred horse country. This past September, Hughes bought several colts at Keeneland Race Course ranging in prices from $300,000 to $500,000 per horse. In April, he paid a record $1.75 million for a two-year-old filly at Keeneland. (Hughes set the prior record for a filly purchase when he paid $1.25 million for Lochlin Slew there.) Other visitors to the area have included Warren Buffett, Queen Elizabeth, Elizabeth Taylor, and fellow billionaire Carl Icahn.

New York Mayor Michael Bloomberg unwinds at his oceanfront estate on Tucker’s Point on the eastern tip of Bermuda. His neighbors are Ross Perot and Michael Douglas, who’ve been spotted at Tucker Point’s golf course. Bermuda is only 21 square miles of island, which keeps the vibe low-key. With crystal clear water, pink sand beaches, and closer proximity to Manhattan than the Caribbean could ever afford, how could Hizzoner ask for anything more?

True, you can find the kinds of designer shops that line Worth Avenue in just about any ritzy urban district, but Palm Beach was always more about parties and high society than shopping. It all started in 1892 when Standard Oil chief Henry Flagler brought the railroad to Florida and started building. It wasn’t long before the Vanderbilts breezed into the new town. Today, billionaire oil titan David Koch owns the 25,000 square-foot oceanside Villa el Sarmiento in this wealthy enclave, and Koch and his wife Julia hold charity galas at their estate. But the barrier island town empties out of boldfaced names before the onset of the steamy Florida summer.

You don’t have to ski to have a good time in Aspen, Colorado, but it wouldn’t hurt. How else are you going to hobnob with Michael Dell on the Silver Queen Gondola, which makes a 14-minute run from Durant Street to the summit of Aspen Mountain? In recent years the dot-com crowd has eroded Hollywood’s monopoly on Rocky Mountain chic, with billionaire Michael Dell, founder of Dell Inc., and his Aspen chalet providing a prime example.

One place where Rupert Murdoch finds his bliss is at Cavan, his vast sheep-station on the banks of the majestic meandering Murrumbidgee River near Yass, New South Wales, Australia. In fact, Murdoch’s son Lachlan married Australian actress/model Sarah O'Hare on the property in 1999. “When you want a truly a fantastic break, the country provides the tranquility and isolation in the most gorgeous pristine, untouched environment,” says Stuart Blackwell, senior winemaker at St. Hallett and one of Australia’s leading vintners.

When he needs to unplug, Bill Gates heads to the dreamy Mnemba Island Lodge in the Indian Ocean. Located on its own private island (whose name means “head of the octopus” in Arabic) three miles from the northeast coast of Zanzibar, the lodge’s guest quarters are comprised of just ten bandas built from woven and thatched palm leaves and other local materials. The powdery white sand beaches are surrounded by magnificent coral reefs, which make for spectacular snorkeling and scuba diving (in fact, turtles lay their eggs there throughout the year). Considered one of the world’s most romantic ocean destinations in the world, at night guests dine by candlelight at the water’s edge.

Wal-Mart heiress Alice Walton spends most of her time at her 3,200-acre Rocking W Ranch in Mineral Wells, Texas, about one hour west of Fort Worth. Devoted to raising champion cutting horses, she is also a keen art collector and watercolorist. Named for its mineral springs, the town gained acclaim as one of the first health resorts in Texas. And everyone is encouraged to drink the mineral waters. Famous past visitors include Clark Gable and Judy Garland.

Las Vegas property developer Sheldon Adelson shuttles between his homes in Malibu, Las Vegas, Newton, Massachusetts, and Tel Aviv on his Boeing jet. But his Tel Aviv abode holds a special place in his heart—perhaps because his physician wife, Miriam was born in the city and graduated magna cum laude from Tel Aviv University's medical school. Considered to be the Mediterranean town that never sleeps, Tel Aviv is Israel’s cultural and financial hub with trendy restaurants, nightclubs and a magnificent stretch of coast.