While it's unimaginable that the energetic star and media mogul ever takes much vacation time, when she does it's sure to be at her estate in Maui, where she owns hundreds of acres. Located in Kula, Oprah's renovated farmhouse overlooks the Pacific coast on about 60 acres. She's not the only star to have invested in a Hawaiian paradise; other celebrities like Randy Travis and Kelsey Grammar also have manses in Maui while Drew Barrymore and Ben Stiller (#55) have their own homes in Kauai.
Following in the footsteps of golf legends Arnold Palmer and Jack Nicklaus, Tiger Woods—just 32 years old and already a mainstay on the Forbes Celebrity 100 list—is trying his hand at designing his own courses. When it's completed in 2009, the Al Ruwaya in Dubai (the name means "serenity" in Arabic) will be a 7700-yard, par-72 championship course that's attached to a five-star luxury resort and exclusive residential community. He'll keep a residence on the grounds, which features full concierge services, a luxury spa and, of course, optional golf memberships for the homeowners
Whether it's adopting babies in Africa or visiting the troops in Iraq, these A-listers know a thing or two about travel. Sometimes, though, a family of six just wants to have fun. This winter, the Jolie-Pitt clan took their private 14-seat plan to Mammoth Mountain in California's Eastern Sierra Nevada range. No word on whether they'll return to camp or bike in the surrounding Inyo National Forest. Of course, by then, the family will need a bigger tent—at press time Jolie was days away from delivering twins.
It was an afternoon that would make any paparazzo sweat. To celebrate her 34th birthday on April 17, 2008, Victoria "Posh Spice" Beckham and husband David hopped aboard Tom Cruise and Katie Holmes' private Gulfstream jet for a few kid-free days in Napa Valley. Some friends came along, too—namely Heidi Klum (#78) and Seal, and Kate Beckinsale with husband Len Wiseman. The octet enjoyed a private winery tour followed by dinner at Thomas Keller's famed French Laundry restaurant. While Napa makes for a nice getaway, TomKat's major rest stop is their isolated home near Telluride, the Colorado ski town that's attracted other power-players such as Oprah (#1) and Oliver Stone.
Georgica Pond may be the most modestly named strip of elite coastline in the U.S. The banks of this lagoon that separates East Hampton and Wainscott have also been owned by the likes of Ron Perelman and Martha Stewart. In 2008, Spielberg bought an additional lot in East Hampton for around $20 million, reportedly in order to just have more privacy. The director uses the home for both business and pleasure, having once hosted the Clintons there and another time flying in Will Smith (#11) via helicopter to offer him the part in Men in Black.
While the press joked that Johnny Depp was taking his role as Captain Jack Sparrow too seriously, it was actually his late friend Marlon Brando who inspired the Pirates of the Caribbean star to buy Little Hall's Pond Cay in the Bahamas. This 35-acre island is completely self-sufficient and, thanks to the protected coral reefs that surround it, completely private. Depp may be turning the Cay into a refuge for other troubled celebs. According to The Boston Globe, while backstage at the 2008 MTV Movie Awards, Depp urged Lindsay Lohan to escape the madding crowds of paparazzi by visiting this little piece of private paradise.
To ring in 2008, Madonna, husband Guy Ritchie, two-year-old son Banda and five friends arrived in Rajasthan, India, on a private jet from the Maldives. They were greeted by the Maharajah of Jodhur himself, and taken on a private five-day tour that reportedly cost $200,000. Highlights included a visit to a traditional village near Jodhpur, luxury tent camping in a nearby wilderness park and one night each at the Sardar Samand heritage hotel and Ummed Bhawan Palace. The trip ended in Mumbai, where the group visited the capital city's impoverished areas—leading to speculation that Madonna and Guy's next adoption will involve an Indian baby.
Jay-Z and Sean "P. Diddy" Combs (#33) may battle for the top "rap mogul" spot on the Forbes Celebrity 100, but the rivalry doesn't affect their real-life friendship. In 2007, Jay-Z and then-girlfriend Beyonce were snapped on Combs' megayacht in the south France. The press had a field day when the duo strolled along the famously nude beach of Saint-Tropez—fully clothed. Shortly after their marriage, Mr. and Mrs. -Z were spotted on the S.S. Diddy again, during the 2008 Cannes Film Festival in May. And this crew doesn't party alone—Lindsay Lohan and Naomi Campbell were just two of the boldfaced names who hopped on-board.