Complex sentence: The pair had left Jordan to vacation in Lebanon on September 29, and had not been heard from since October 1, when they told a friend they were leaving Beirut to travel to the northern town of Tripoli via Byblos.
Split into simpler sentences: The pair had left Jordan to vacation in Lebanon on September 29. On October 1 they told a friend they were leaving Beirut to travel to the northern town of Tripoli via Byblos.