While his older brother, then-Prince Charles, was preparing for life as the reigning monarch and working alongside the late Queen Elizabeth II, Prince Andrew wasn't taking his royal role so seriously. In the early 2000s, Andrew was known for being away for days at a time on incredible vacations, joining the likes of Jeffrey Epstein and Ghislaine Maxwell and the elite social circle they used to be a part of. It was reported that during a trip to Phuket, Thailand, in 2000, Andrew spent about $4,800 a night on an incredibly exclusive resort. To really seal the deal on just how lavish — and frivolous — his trip was, Andrew was photographed with half-nude women while on the trip, enjoying the splendors of a private yacht.

In addition to his trip to Thailand, Andrew also traveled to New York, Florida, and the Caribbean — specifically St. Tropez — to continue rubbing shoulders with the world's elite, collectively spending thousands. He reportedly traveled with his mattress, a personal manicurist, and his valet with him. He also enjoyed champagne that costs hundreds of dollars with his friends while partying at nightclubs. It certainly is a quality of life that very few enjoy — and given his missteps, Andrew certainly doesn't have the friends he once used to.