What does Acts 27:16 mean?
ESV: Running under the lee of a small island called Cauda, we managed with difficulty to secure the ship 's boat.
NIV: As we passed to the lee of a small island called Cauda, we were hardly able to make the lifeboat secure,
NASB: Running under the shelter of a small island called Cauda, we were able to get the ship’s boat under control only with difficulty.
CSB: After running under the shelter of a little island called Cauda, we were barely able to get control of the skiff.
NLT: We sailed along the sheltered side of a small island named Cauda, where with great difficulty we hoisted aboard the lifeboat being towed behind us.
KJV: And running under a certain island which is called Clauda, we had much work to come by the boat:
NKJV: And running under the shelter of an island called Clauda, we secured the skiff with difficulty.
Verse Commentary:
An Alexandrian ship, likely exporting grain, is on its way to Rome, carrying Paul, Luke, and Aristarchus. But after making it to Fair Havens on the southern shore of Crete, the crew realized they needed to find a place to stay for the winter. Fair Havens isn't suitable. The ship's owner and pilot decided to try for Phoenix, about 40 miles, or 64 kilometers, to the west. Paul warned them it was a bad idea. They left Fair Havens, sailed west, rounded a point, and headed straight for Phoenix. As soon as the terrain turned flat, however, the winds changed. A "tempestuous" nor'easter caught them (Acts 27:14) and drove them southwest toward Cauda.

Cauda is a small island south of Phoenix; today it's called Gavdos. The hills aren't nearly as high as on Crete, but it protects the ship just enough to allow the crew to prepare for what is to come. The "ship's boat" is a skiff used to take passengers to shore if there's no deep port. It's usually tied behind the ship and dragged along, but by this time the wind and waves probably either capsized it or filled it with water.

Once the skiff is secured, the sailors reinforce the ship by stringing ropes under the hull. They quickly realize they're headed for the Syrtis: a gulf near Libya well known for hidden shoals. These shallow sandbars can strand a ship far from the shore. The shallower the ship sits in the water, the more likely they'll clear the shoals. To lighten the ship and raise the keel, the crew throws some cargo into the sea. To try to slow down, they lower the sails to the deck and toss some of the ship's tackle overboard, probably to act as a sea anchor. Despite their precautions, the crew knows it's not going to be enough and abandon hope of surviving (Acts 27:17–20).
Verse Context:
Acts 27:13–20 switches Luke's narrative back from Paul to the sea voyage. Paul, Aristarchus, and Luke are on a ship for Rome, but the winds keep pushing them south. They've reached a harbor to wait out the winter and Paul wants to stay. The crew refuses. They set sail and promptly hit a powerful wind which pushes them into a typhoon-like winter storm. The sailors do what they can to stay afloat, but the storm rages for days. The passengers and crew lose hope, but Paul doesn't (Acts 23:11).
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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