There was war between Aretas, who reigned at Petra, the desert metropolis of Stony Arabia, and Herod Antipas, his son-in-law, the Tetrarch of Galilee. A misunderstanding concerning the boundaries of the two principalities had been aggravated into a quarrel by Herod’s unfaithfulness to the daughter of the Arabian king, and his shameful attachment to "his brother Philip’s wife." It is evident that the relations of the neighboring powers must have been for some years in a very unsettled condition along the frontiers of Arabia, Judea, and Syria. The falling of a rich border town like Damascus from the hands of the Romans into those of Aretas would be a natural occurrence of the war.
No journey was ever taken, on which so much interest is concentrated, as this of Apostle Paul from Jerusalem to Damascus. It is difficult to guess what was the appearance of Saul’s company on that memorable occasion. We neither know how he traveled, nor who his associates were, nor where he rested on his way, nor what road he followed from the Judean to the Syrian capital of Damascus.
Paul's journey to Damascus must have brought him somewhere into the vicinity of the Sea of Tiberias. But where he approached the nearest to the shores of this sacred lake, whether he crossed the Jordan where, in its lower course, it flows southwards to the Dead Sea, or where its upper windings enrich the valley at the base of Mount Hermon, we do not know. And there is one thought which makes us glad that it should be so. It is remarkable that Galilee, where Jesus worked so many of His miracles, is the scene of none of those transactions which are related in the Acts. The blue waters of Tiberias, with their fishing boats and towns on the brink of the shore, are consecrated to the Gospels. A greater than Paul was here.
When we come to the journeys of the Apostles, the scenery is no longer limited and Jewish, but universal and widely extended, like the Gospel which they preached. The Sea, which will be so often spread before us in the life of Apostle Paul, is not the little Lake of Genesareth, but the great Mediterranean, which washed the shores and carried the ships of the historical nations of antiquity.
Two principal roads can be mentioned, one of which probably conducted the travelers from Jerusalem to Damascus. The track of the caravans, in ancient and modern times, which undertook the journey from Egypt to the Syrian capital, has always led through Gaza and Ramleh. They then turn eastwards about the borders of Galilee and Samaria, and descend near Mount Tabor towards the Sea of Tiberias. The road then crosses the Jordan a little to the north of the Lake by Jacob’s Bridge, then proceeds through the desert country which stretches to the base of Antilibanus. A similar track from Jerusalem falls into this Egyptian road in the neighborhood of Djenin, at the entrance of Galilee. Paul and his company may have traveled by this route.
At this period, that great work of Roman road making, which was actively going on in all parts of the empire, must have extended, in some degree, to Syria, Judea and even to Damascus. If the Roman roads were already constructed here, there is little doubt that they followed the direction indicated by the later itineraries. This direction is from Jerusalem to Neapolis (the ancient Shechem), and thence over the Jordan to the south of the Lake, near Scythopolis, where the soldiers of Pompey crossed the river, and where the Galilean pilgrims used to cross it, at the time of the festivals, to avoid Samaria. From Scythopolis it led to Gadara, a Roman city, the ruins of which are still remaining, and the proceeded a bit farther before the journey ended in Damascus.