Season 1

On a hill above Malibu, California, the cast gathers as a helicopter dumps a suitcase. Inside the case lies a tape with a tape player and five plastic bags. Mark, Shelley, Alison, Kit, and Carlos are instructed to stash all their cash and credit cards in the bags and follow the dirt road to their Winnebago. Their first clue directs them to drive to Ivan Powah Lake in Nevada to obtain one sail before the big race. After they get lost, they arrive at Ivan Powah, where their mission is to landsail on a dried lake. The first two finishers will earn hotel rooms at Excalibur in Las Vegas. Mark finishes first and Carlos finishes second. In Las Vegas they receive a clue guiding them to meet the youngest mayor in America in Nogales, Arizona. Upon arriving in Nogales, they are instructed to participate in a Pentathalon, which makes them nervous.