What does Acts 27:8 mean?

Paul, Aristarchus, and Luke are on a ship headed for Rome. Paul and Aristarchus are prisoners in the custody of a Roman centurion who is taking them to trial in Caesar's court. Luke is along for the ride. They launched from the southwest coast of modern-day Turkey and are now hugging the southern coast of the island of Crete on the southern edge of the Aegean Sea. The winds have been against them the whole way (Acts 27:1–7).

The ship is likely an Alexandrian wheat ship. Rome requires around 175,000 tons, or about 160 million kilograms, of wheat each year. Most of this comes from Alexandria, Egypt. Wheat ships of Paul's era are up to 180 by 50 feet wide, or 55 by 15 meters, and almost as tall as they are wide. For reference, this is about the size of a large modern sea-going tugboat.

Despite the winds, they reach Fair Havens just past Lasea about halfway along the coast. Lasea has a good harbor to winter in, but Fair Havens doesn't. It's unclear why they don't go back to Lasea. Paul tells the officers of the ship and the centurion they should winter in Fair Havens, regardless. The owner of the ship and his pilot convince the centurion it's too dangerous; they would be better continuing west to the port at Phoenix (Acts 27:9–12). They never make it (Acts 27:41). They barely leave the port before the nor'easters drive them toward Libya. They barely miss the shallow reef there before the winds drive them northwest where they wreck on the coast of Malta.

The centurion does get his prisoners to Rome—by the grace of God—and learns to trust Paul along the way.