Dapeng Bay National Scenic Area, the fourth national scenic area in Taiwan, is featured as an international tourism and leisure zone. A national regatta has been conducted every year, in which the participating sailboats have to race between Dapeng Bay and the nearby island of Little Liuqiu. Maritime weather and ocean conditions are very important preconditions for marine recreations, especially for sailing activity. In this paper, meteorological and oceanic information, collected from two data buoys deployed by the Central Weather Bureau and the Dapeng Bay National Scenic Area Administration, were analyzed to determine the appropriate season and time for holding the regatta. Hourly recorded data, including wind speed and direction, significant wave height, air and sea surface temperature, and barometric pressure, were first considered statistically. The racing rules and management policies of sailing competition, proposed by the International Sailing Federation, were then referred to examine the conditions of wind velocity and direction as well as wind shift. The results show that the local wind rarely reached the risky condition, timely changes are more important consideration than seasonal variations, and summer is more suitable season than winter for the sailboat racing. However, typhoons should be taken into account, because they visited Taiwan every summer. Finally, we conclude that April, May and June are the best months for holding sailboat racing in this area. In consideration of hourly wind condition, it is better to start the racing in the afternoon. Furthermore, the local condition of Dapeng Bay is better than Little Liuqiu to hold a confined boat race competition.