"And when it was decided that we should sail to Italy, they delivered Paul and some other prisoners to one named Julius, a centurion of the Augustan Regiment. So, entering a ship of Adramyttium, we put to sea, meaning to sail along the coasts of Asia. Aristarchus, a Macedonian of Thessalonica, was with us. And the next day we landed at Sidon. And Julius treated Paul kindly and gave him liberty to go to his friends and receive care. When we had put to sea from there, we sailed under the shelter of Cyprus, because the winds were contrary. And when we had sailed over the sea which is off Cilicia and Pamphylia, we came to Myra, a city of Lycia. There the centurion found an Alexandrian ship sailing to Italy, and he put us on board. When we had sailed slowly many days, and arrived with difficulty off Cnidus, the wind not permitting us to proceed, we sailed under the shelter of Crete off Salmone. Passing it with difficulty, we came to a place called Fair Havens, near the city of Lasea" (Acts 27:1-8).
It is unknown how much time passed between Paul's examination before Agrippa and the sending of Paul by Festus to Rome in Italy. The use of the pronoun "we" in Acts 27:1ff is a clear indicator of Luke's presence. At the very least, Paul has two friends who are fellow travelers as this journey begins (Luke and Aristarchus). Paul, as well as some other prisoners, was put under the care of a centurion named Julius. Julius was kind to Paul along their journey, obviously realizing Paul was an ideal prisoner and posed no flight risk.
Luke records the various cities they came to on their journey and is quick to point out the difficulty they had with the wind. The contrary wind made their journey very slow and challenging--almost impossible at times. Their slow progress would cause another problem from them. As a side note, much of what Luke wrote in Acts 27 is checkable and has been verified. The fact that every checkable matter always shows Luke to be an exceptionally accurate historian lends credibility to his comments that cannot be examined in the modern age. God's word is true and reliable!
"Now when much time had been spent, and sailing was now dangerous because the Fast was already over, Paul advised them, saying, 'Men, I perceive that this voyage will end with disaster and much loss, not only of the cargo and ship, but also our lives.' Nevertheless the centurion was more persuaded by the helmsman and the owner of the ship than by the things spoken by Paul. And because the harbor was not suitable to winter in, the majority advised to set sail from there also, if by any means they could reach Phoenix, a harbor of Crete opening toward the southwest and northwest, and winter there" (Acts 27:9-12).
Luke's reference to "the Fast" would have been the Day of Atonement (which would fall in late September or early October on our calendar today). Conditions for sea travel in that region always deteriorated even further as winter approached. The winds had crippled their progress and it would only get worse. Paul, aware of Julius' determination to get to Rome sooner rather than later, gives an uninspired opinion when declaring - "I perceive that this voyage will end with disaster and much loss, not only of the cargo and ship, but also our lives." Paul made this statement based on his past experiences and observations, not prophecy. He fears they are going to make a foolish decision rather than waiting for Spring, which would have been the safe time to complete their journey. Paul's speculation turns out to be mostly correct. They would suffer much loss, though no one would die.
The centurion, Julius, decides to keep sailing for now, hoping to reach Phoenix and stay there for the winter. Julius doesn't yet appreciate the apostle like he will in the future. For now Julius is persuaded to take to the advice of the helmsman and ship owner. This proves to be a costly mistake.