In October 2003, sixteen boats set off from La Gomera in the Canary Islands headed for Barbados 4800 km distant. Each boat was manned by two oarsmen who were competing in the Transatlantic Challenge, an ocean rowing endurance event. This paper describes an optimization model developed for route planning in this event. It was used successfully by the Holiday Shoppe team to win the race in world record time. We describe the tool, its history, and the way it was used in the race.