We are told that it was only with great difficulty that the vessel was able to get around the cape at the eastern extremity of Crete to gain shelter from the strong sea winds out of the northwest (Acts 27:7-8). Not long afterward they were able to sail into the port of Fair Havens. Considering the late time of the year and the fact that already the vessel had been struggling against the prevailing winds in this arduous journey, one might expect the captain to want to winter at this harbor that seemed to promise safety for both lives onboard and the ship’s cargo. In fact, this is exactly what is behind Paul’s argument (cp. Acts 27:9-10).
This begs the questions: first, why would the opinion of a prisoner such as Paul be taken seriously, and, second, why would the captain and crew desire to continue the laborious journey when they knew the sea was dangerous for both their lives and the ship’s freight, especially when they seemed safe where they were presently docked?
To begin with, not only should Paul’s opinion be taken seriously, but as an uncondemned Roman citizen, he probably outranked everyone on board the vessel except for Julius, who was also, undoubtedly, a Roman citizen. Aristides (Orations 50:32-27) and Cicero (Epistulae ad Familiars, 16.9.4) both suggest that “decisions whether to sail or not were not usually left up to the sailing professionals.” Therefore, it may very well have been that as an equal to Julius, the centurion, Paul’s advice may have been sought, not simply offered without invitation. Nevertheless, Julius who seems to have had the final decision as an officer in Caesar’s army, opted in agreement with the professionals.
The reason given for continuing on their journey by Luke in Acts 27:12 is that the Fair Haven port wasn’t suitable to winter the large grain vessel, but it should be understood by the reader that the captain (and crew?) offered this as the reason they should continue to sail westward. But, is this reason really accurate? Some would argue against such a position:
“Fair Havens is so well protected by islands that, though not equal to Lutro [a port farther west along the coast], it must be a very fair winter harbor; and that considering the suddenness, the frequency, and the violence with which gales of northerly wind spring up, and the certainty that, if such a gale sprang up in the passage from Fair Havens to Lutro, the ship must be driven off to sea, the prudence of the advice given by the master and owner was extremely questionable, and that the advice given by St. Paul may probably be supported even on nautical grounds.” (James Smith, The Voyage and Shipwreck of St. Paul, page 85n; quoted from F.F. Bruce, The Acts of the Apostles, page 507).
If the above is true, one may, indeed, wonder why the owner/captain (and crew?) of this vessel was so willing to continue the already arduous journey any further, knowing the danger this time of year presented on the open sea. The probable motive points to commercial profit. Urban Rome was periodically subject to food shortages. In fact, famines in Rome nearly resulted in sedition against Claudius at one point, and he afterward guaranteed insurance coverage for the loss of ships and offered a special bounty for shipments that braved the sea in the hazardous winter months; and these incentives and promises continued during the reign of Nero. So, one is able, not only to see the logic behind such late sea voyages, but one also has to wonder if the captain and crew really intended to winter at the ‘more favorable’ harbor, or would they want to move on if fair weather continued?
 See Ben Witherington, The Acts of the Apostles, page 763 note
 See Suetonius, Life of Claudius 18:1-2, cited by Luke Timothy Johnson in The Acts of the Apostles.