Each 6×30-min episode sees a pair of celebrity friends or colleagues embark on a holiday destination or city break where each traveler will get to enjoy a very different vacation experience. At the departure airport they will choose envelopes, with one traveler set to enjoy the 5-star luxury treatment including a limo, restaurants and activities galore while the other gets to experience the exact opposite - a budget break with no frills in the same destination. During the programme, the pair will meet up regularly to experience each other's holiday and compare and contrast who really drew the short straw.