Lili regenerated near Jamaica on the evening of September 26 and gradually turned more to the west-northwest while strengthening. The system became a hurricane on September 30, just after passing through the Cayman Islands. The storm continued on its course while continuing to intensify, and made landfall twice the next day, on the Isle of Youth and near Pinar del Río as a Category 2 hurricane. Lili emerged over the Gulf of Mexico later that day, having lost little strength during its overland passage.