Jacoby competed in the 1987
Coast to Coast adventure race in New Zealand's
South Island in the two-day team event with fellow Australian Andrew Maffett, coming in second place. In the following, Jacoby entered the "Longest Day" category of the event, competing in the race as an individual and completing the of mountain running, road cycling, and river kayaking within one day. Maffett was his support person. The leading competitor had five minutes on Jacoby entering the river, but Jacoby had turned this into a 14-minute lead leaving the river. Jacoby won the event with the same lead over
Steve Gurney, in a time of 12:02:59 hours. He narrowly missed out on winning a
NZ$35,000
Ford Laser TX3 Turbo, which was the price for the first competitor to break the 12-hour mark. Jacoby would win the Coast to Coast on two subsequent occasions: in 1989 and in 1993. In 1991, he came in third place. Jacoby rates the Coast to Coast as one of his favourite competitions. Jacoby competed in the 2004 Subaru
Primal Quest. There was a rockfall that killed fellow competitor Nigel Aylott; the same rock hit Jacoby at the leg and put him into hospital. In August 2015, Jacoby and fellow adventurer Brian Freeman paddled across the
Bass Strait within 60 hours unsupported from
Wilsons Promontory in Victoria to Little Musselroe Bay in
Tasmania. ==Notes==