Acts 27:1-12

1When it was decided that we would sail for Italy, Paul and some other prisoners were handed over to a centurion named Julius, who belonged to the Imperial Regiment. 2We boarded a ship from Adramyttium about to sail for ports along the coast of the province of Asia, and we put out to sea. Aristarchus, a Macedonian from Thessalonica, was with us.

3The next day we landed at Sidon; and Julius, in kindness to Paul, allowed him to go to his friends so they might provide for his needs. 4From there we put out to sea again and passed to the lee of Cyprus because the winds were against us. 5When we had sailed across the open sea off the coast of Cilicia and Pamphylia, we landed at Myra in Lycia. 6There the centurion found an Alexandrian ship sailing for Italy and put us on board. 7We made slow headway for many days and had difficulty arriving off Cnidus. When the wind did not allow us to hold our course, we sailed to the lee of Crete, opposite Salmone. 8We moved along the coast with difficulty and came to a place called Fair Havens, near the town of Lasea.

9Much time had been lost, and sailing had already become dangerous because by now it was after the Fast. So Paul warned them, 10"Men, I can see that our voyage is going to be disastrous and bring great loss to ship and cargo, and to our own lives also." 11But the centurion, instead of listening to what Paul said, followed the advice of the pilot and of the owner of the ship. 12Since the harbor was unsuitable to winter in, the majority decided that we should sail on, hoping to reach Phoenix and winter there. This was a harbor in Crete, facing both southwest and northwest.

According to my commentary

Ships in ancient times had no compasses and navigated by the stars. Overcast weather made sailing almost impossible and very dangerous. Sailing was doubtful in September and impossible by November. This event occurred in October (A.D. 59)

Although this was not the best time to sail the pilot and the owner of the ship didn't want to spend the winter in Lasea, and so the pilot took a chance. At first the winds and weather were favorable, but then the deadly storm arose.