Tom Cruise (#31) and David Beckham (#5): Napa Valley, Calif.

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.