Luke commences Paul’s journey to Rome by resuming the we passages that he left off using in Acts 21:18 at Jerusalem. It had been argued that the we passages simply refer to the people in the boat and immediately afterward on land, but this doesn’t seem to fit. For example, Luke continued to use the first and third person plural in passages on land from Acts 21:4 to 21:18, a time-span of over two weeks. Moreover, in Acts 27:1 Luke says: “When it was determined that we should sail to Italy…” At this point Paul and company weren’t on the vessel they hoped would bring them to Italy. Neither the captain of this vessel nor its crew would go to Italy. The ship Paul boarded was a coasting vessel that hugged the shore line, while making stops at several ports where it unladed its cargo and perhaps took on more. Eventually, the centurion with Paul was able to find a seaworthy vessel that could take them to Italy at Myra of Pamphylia (Acts 27:6).
Travelling with Paul were Luke, implied in the we passages as author of the book of Acts, and Aristarchus, of Macedonia. Some believe Aristarchus didn’t continue with Paul to Rome but went home when the centurion transshipped to the larger Alexandrian vessel at Myra. This may be so, providing Paul’s letters to the Colossians and Philemon were written from Caesarea (cp. Colossians 4:10 and Philemon 1:24), but if he wrote them from Rome, it is unlikely that Aristarchus left Paul at Myra. In any event, it seems as though Aristarchus stayed with Paul for over three years, while Paul was under house arrest at Caesarea, for he came with him on his journey to Jerusalem with the gift from the gentile churches (cp. Acts 20:4).
Paul was treated very well by the centurion, Julius. When the ship came to Sidon, Paul was permitted to go to his friends and be refreshed (Acts 27:3). This presumes there was a church in Sidon (cp. Acts 11:19) where Paul was able to withdraw to while the ship loaded or unloaded its cargo. Naturally, Paul would have been under guard, but as a Roman citizen, uncondemned, this was not an unreasonable act. Moreover, this is one of the instances in late Acts where Luke implies Paul had or had recently come into some wealth. Some scholars argue for reconciliation with his father who arguably was a man of means, and we must not forget that Luke ends his thesis with Paul preaching for two years out of his own rented house. One has to wonder how he obtained the funds to do so, if he was unable to labor with his hands and given his policy to refuse support from those to whom he preached. Nevertheless, believing Paul was a man of means would have enhanced his position in the eyes of the Julius, the centurion. After all, how serious would a penniless traveler be taken either in the 1st century CE or the 21st? Yet, Paul was not only treated well by Julius, but for all intents and purposes was given command of the vessel before the journey’s end.
The ship chosen by the centurion to take Paul and the other prisoners to Rome was an Alexandrian grain vessel (Acts 27:6). The voyage on the larger ship seemed doomed from the start, for Luke tells us in Acts 27:7 that it took many days to travel from Myra to Cnidus, the western extremity of the province of Asia, and the last point of the mainland which protected the ships from strong sea winds out of the north. Considering it took Paul five days to travel from this vicinity to Tyre (Acts 21:1-3) but many days from Myra to Cindus (about a day’s travel by sea), Luke seems to be saying that adverse weather conditions delayed the voyage by several days—or about two or three additional days. From Cnidus, the captain had a choice. He could either wait in the suitable Cnidus harbor for favorable winds to take him directly west across the Aegean, or he could head southwest for the island of Crete and sail under its lee. The latter was chosen, for, as we’ll see later, the captain of the vessel was in a hurry to reach Rome.
 See F.F. Bruce, The Book of Acts, page 421, citing Chrysostom (Homily xlv.2).