New York mayor Michael Bloomberg—the 8th-richest American, according to the latest Forbes report—interpreted the old saying "go west, young man" quite literally, when he bought a vacation home in the lavish ski resort town of Vail, Colo. Bloomberg frequently dines at Vail Mountain's exclusive Game Creek Club—where members pay an exorbitant $50,000 initiation fee—with others in his league. But he doesn't like to stick to one spot every time the urge to vacation strikes. He also owns a $10 million Victorian townhouse on London's Cadogan Square, a sprawling Westchester estate in Armonk and a $10.5 million mansion in Tucker's Town, Bermuda, that fronts the ocean. This is when having a private jet comes in handy.

While the workaholic's vacations are few and far between, Viacom owner Sumner Redstone has been known to visit Anguilla in the past, where he had a longer phone cord installed so he could do his work while gazing at the glint of the turquoise blue sea. The most northern of the Leeward Islands, Anguilla houses 33 beaches, often considered among the most beautiful in the Caribbean, and is accustomed to accommodating celebrities, which in the past have included Denzel Washington, Beyonce and Jay-Z.

The Queen of Daytime Television, Oprah Winfrey, hopped a plane to Italy earlier this year, where she and gal pal Gayle King dilly-dallied about the small fishing village and resort town of Portofino, dining alfresco and window shopping. While the Hotel Splendido refused to comment on her most recent visit, she's been known to unwind at the elegant waterfront property in the past. When not enjoying a European holiday, Winfrey has also been a guest at Richard Branson's exclusive Caribbean gem, Necker Island.

Ross Perot first purchased a plot of land in the gated enclave Tucker's Town—where he's neighbors with fellow Forbes 400 member Michael Bloomberg—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. The Perots fly their Gulfstream to Bermuda from their home in Texas; while there, the businessman and former presidential candidate likes to splash about in the water, spending much time on his boats and jet skis.

Nestled on California's central coast a few hours south of San Francisco, Carmel has long been a haven for the rich seeking a quiet refuge. Murdoch (a native Australian but naturalized American) retreats to his family ranch in Carmel Valley a few weeks out of the year and has been known to host dinner parties on the estate that include such guests as Nicole Kidman. He's also been spotted dining at Anton & Michel in Carmel-by-the-Sea, a locals' favorite and—surprisingly—inexpensive French restaurant.

While St. Barts is a favorite hideaway for the celebrity set, it also draws affluent yachters from far and wide to its snow white sand beaches and sparkling water that looks clean enough to drink. Microsoft co-founder Paul Allen is one of the many who dock their boats in the French West Indies, and Allen doesn't even have to worry about being recognized during his entry and exit. Aboard his yacht, Octopus, there's a 10-person submarine, as well as a pair of helicopters. Allen's been known to take his yacht all over the world, with other recent stops in Tahiti, New Zealand and the British Virgin Islands.

While being the CEO of a global conglomerate like Apple can't leave much time for leisurely jaunts, Steve Jobs often whisks his family away from their home in California to Hawaii, where they are frequent guests at the high-end Kona Village Resort. The 82-acre property on the Big Island's Kohala Coast is arranged in thatched-roof, Polynesian-style, oceanfront bungalows that offer the utmost privacy. Jobs might even switch off his iPhone for the occasion, considering the resort prohibits the use of all telephones, televisions and radios.

English business magnate Richard Branson was onto something when he developed Necker Island, a previously uninhabited 74-acre island, into the ultimate luxury getaway. Today, the private retreat features 10 Balinese-style bedrooms and can accommodate 28 guests, and is a favorite vacation spot of Steven Spielberg. But the esteemed director wasn't the first high-profile guest to take a break in paradise. Oprah Winfrey, Mel Gibson, Janet Jackson and Michael Douglas have all spent their free time on Necker in the past. To rent the entire property (the only option) will put you out nearly $50,000 a night. When Spielberg prefers to be a bit more in touch with civilization, he hops a jet to his East Hampton home instead.

Although Seattle-based entrepreneur Craig McCaw purchased Canada's James Island in 1994 as a business endeavor, he also uses it for his own recreational purposes. When McCaw turned 50 several years ago, he hosted one giant soiree on his 780-acre piece of property, complete with a mini replica of his hometown Centralia, Wash., that included clowns, a high school band, vintage cars and baton twirlers on horseback. McCaw has further developed the island into one giant resort playground, with a golf course, seaplane ramp, air strip and yacht moorage—assumedly for his own use (many of McCaw's travels involve yacht races in different corners of the world).

If you're an affluent yachter looking for more of your kind, there's nary a better place to take your boat on vacation than the posh Bitter End Yacht Club in the British Virgin Islands. David Geffen and Larry Ellison,  who co-own the Rising Sun, frequent the Caribbean hotspot; also known to dock their boats at Bitter End are Paul Allen and the McCaw and Dolan families.