This study focus on the optimal time limit of ship-to-ship (STS) liquid natural gas (LNG) bunkering by dynamic simulation. Based on this, a mathematical model for calculating the boil-off gas (BOG) amount was developed. With respect to the modeling of the study, the diameter of the bunkering line is set as 8 inch while that of the BOG return pipeline is set as 4 inch to satisfy the pressure of the receiving ship and BOG generation. The capacities of the cargo tank and fuel tank for bunkering and receiving ships are set as 4538 m3 and 700 m3, respectively. The results indicated that the BOG amount with different LNG bunkering time limit is variable. The BOG flow rate varies inversely with respect to the bunkering time limit after 20 min. Additionally, it is necessary to control the bunkering time within 120 min since additional BOG is generated when the capacity of the pump exceeds 100,000 kg/h, and thus the tank pressure difference between bunkering and receiving ship may be reduced. It is believed that the results of the research could provide feasible assistance for STS LNG bunkering for the ports, and could give a specific guideline for the amount of the BOG generation.