This research, which was conducted with crew members of an America's Cup team, had the following objectives: (a) to assess energy expenditure and intake during training; (b) to evaluate the sailors' diet, and (c) to identify any dietary flaws to determine the appropriate intake of nutrients, correct possible dietary mistakes, and improve their food habits. Energy expenditure was estimated on 15 sailors using direct measurements (oxygen consumption) and a 3-day activity questionnaire. Oxygen consumption was measured on sailors during both on-water America's Cup sailing training and dry-land fitness training. Composition of the diet was estimated using a 3-day food record. Average daily energy expenditure of the sailors ranged from 14.95 to 24.4 MJ, depending on body mass and boat role, with the highest values found in grinders and mastmen. Daily energy intake ranged from 15.7 to 23.3 MJ (from +6% to -18% of energy expenditure). The contributions of carbohydrate, protein, and fat to total energy intake were 43%, 18%, and 39% respectively, values that are not in accord with the recommended guidelines for athletes. Our results show the importance of assessing energy balance and food habits for America's Cup sailors performing different roles. The practical outcome of this study was that the sailors were given dietary advice and prescribed a Mediterranean diet, explained in specific nutrition lectures.