In this study, in order to contribute to the prediction of drifting ships during a typhoon, we examined the variations of size and moving distance of ships located in Tokyo Bay during the typhoon no. 15 and 19 in 2019. As a result of AIS data analysis, moving distance of ships become long if the size of ship is small. We also conducted numerical simulation for reproducing drift of ships which reached the collision during the typhoon no. 15. But time series of ship position could not be reproduced. The averaged wind speed and direnction were reproduced well in our simulation. Thus, it is likely that local wind affects to drifting of ships. In addition, in the case of changing the anchorage position, the result was that the collision was evaded considering the drift distance and wind field at that time.