What does Acts 27:4 mean?
Paul is on his way to Rome, a prisoner being transported to a higher court. He's completely innocent, and both Governor Festus and King Agrippa II know it. However, Paul has appealed his case to Caesar, so they must send him (Acts 26:31–32). Aristarchus, a Jew from Thessalonica in Macedonia, is Paul's fellow prisoner (Colossians 4:10) while Luke is traveling with them. The men boarded a ship in Caesarea Maritima, the Roman capital of the district, and are headed to Myra on the southern coast of modern-day Asia Minor (Acts 27:1–2, 5).In Sidon, the centurion who guards the prisoners let Paul's friends tend to his needs (Acts 27:3). Now they sail northwest toward northeast Cyprus. From Caesarea, Myra is directly northwest, but the strong winds would hit them straight on. It's easier to hug the shores of southern Asia Minor where the mountains can break up the winds. "Under the lee" or "under the shelter" (NASB, NKJV) here means the eastern side. Cyprus also has a mountain range on its southern coast, but once clear the ship would be traveling headlong into those winds.
When the ship gets to Myra, the centurion will find a ship headed to Rome. Before long, he will realize why it is much safer to travel over land. After a harrowing few weeks in fierce conditions and a shipwreck that completely destroys the ship, Paul and his companions will finally get to Rome.