What does Acts 27:4 mean?
ESV: And putting out to sea from there we sailed under the lee of Cyprus, because the winds were against us.
NIV: From there we put out to sea again and passed to the lee of Cyprus because the winds were against us.
NASB: From there we put out to sea and sailed under the shelter of Cyprus, because the winds were contrary.
CSB: When we had put out to sea from there, we sailed along the northern coast of Cyprus because the winds were against us.
NLT: Putting out to sea from there, we encountered strong headwinds that made it difficult to keep the ship on course, so we sailed north of Cyprus between the island and the mainland.
KJV: And when we had launched from thence, we sailed under Cyprus, because the winds were contrary.
NKJV: When we had put to sea from there, we sailed under the shelter of Cyprus, because the winds were contrary.
Verse Commentary:
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.
Verse Context:
Acts 27:1–8 records the first leg of Paul, Luke, and Aristarchus's sea voyage to Rome. After two governors refused to give Paul justice, he appealed his case to Rome. The trio board at Caesarea Maritima under the custody of Julius, a centurion. After changing to a larger ship, the weather turns uncooperative in Myra and the winds blow the ship into a ferocious storm. Paul spends the voyage reassuring the passengers and encouraging the crew to make wise choices. They eventually crash on the island of Malta: the ship and cargo are destroyed, but everyone lives.
Chapter Summary:
Acts 27 is an account of a famous sea voyage. Paul, Luke, and Aristarchus travel from Caesarea Maritima on their way to Rome. False charges and two years of imprisonment in Caesarea led Paul to appeal his case to a higher Roman court, and he is now on his way to that court. The chapter can be divided into seven paragraphs, alternating between descriptions of the sea voyage and Paul trying to keep everyone alive during a horrific storm. Eventually, they shipwreck on Malta. The ship and cargo are a complete loss, but no one dies.
Chapter Context:
Twice the Sanhedrin brought unfounded charges against Paul. In both cases, the ruling governor knew Paul was innocent but refused to let him go. Finally, Paul appealed his case to Caesar (Acts 24:22–27; 25:1–12). He, Luke, Aristarchus, and 273 others sail for Rome. But they shipwreck on a reef off the island of Malta. When they finally reach Rome, Paul will meet with Jewish leaders and tell them how Jesus fulfills the Old Testament prophecies of the Messiah. Some will believe and some won't. This leads Paul to resolve, once again, to focus his efforts on the Gentiles (Acts 28).
Book Summary:
The summary of the book of Acts is provided in Jesus' words in Acts 1:8: ''But you will receive power when the Holy Spirit has come upon you, and you will be my witnesses in Jerusalem and in all Judea and Samaria, and to the ends of the earth.'' In Acts 2:1–13, the Christ-followers receive the Holy Spirit. Acts 2:14—7:60 describes the rapid growth of the church in Jerusalem. Chapters 8—12 find Jewish persecution inadvertently spreading the gospel throughout Judea and Samaria. And in chapters 13—28, Paul and his companions spread the good news throughout the Roman Empire.
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