This study combines whole farm economic analysis with biophysical simulation techniques in order to achieve a twofold objective. First, the study seeks to develop a multiple enterprise vegetable farm model with a production and marketing decision interface and, second, to determine optimal production practices for Kentucky vegetable growers. Three vegetable crops are examined: tomatoes, bell peppers and sweet corn. The findings indicate that the risk associated with vegetable production can be significantly mitigated with diversification of production mix and with a greater number of transplanting dates. However, this reduction in risk comes at a high cost in terms of expected net returns.