Jack travels to the Canadian Rockies with Natalie Imbruglia, Billy Boyd and Konnie Huq for a series of different challenges. Firstly they have to climb Mount Fable but they soon find themselves in difficulties. They also go mountain biking in some woods and experience underground caving.

Natalie Imbruglia, Billy Boyd and Konnie Huq travel to Hawaii with Jack. Whilst there they try out free diving and they then go on a kayaking trip along the remote volcanic coastline. A the end of their trip they try out surfing.