In 60 A.D., after spending roughly two years in Caesarea's prison, Paul requests that Roman Governor Festus send him to Rome to have the case against him heard by Caesar. Festus obliges him and soon a Roman soldier named Julius is charged with taking him to the empire's capital. Julius befriends the apostle and allows certain liberties such as seeing Paul's friends in Sidon.
. . . they delivered up Paul and certain other prisoners to a centurion named Julius, who was of the band of Augustus . . . And Julius treated Paul kindly, allowing him to go to his friends to refresh himself (Acts 27:1, 3).
The first part of Paul's journey to Rome is somewhat uneventful. After boarding another ship in Myra bound for Italy, however, the trip begins to take a turn for the worse. The ship leaves Myra with 276 total people aboard her (Acts 27:37). Since strong winds forbid the vessel from sailing in a westerly direction directly toward Italy, it sails South toward the shelter of the island of Crete.
. . . so we sailed down the sheltered side of the island of Crete, passing by Cape Salmone. We kept close to the coast and with great difficulty came to a place called Safe Harbors (called 'Fair Havens' in other translations), not far from the town of Lasea. (Acts 27:7 - 8).
The ship docks for a short period in Fair Havens until it is after the holy day known as the Day of Atonement (an annual Feast day of God), which fell in 60 A.D. on September 24th.
The optimal period for navigating the Mediterranean Sea was, in the first century, from April to October. Because of the winds, stormy weather and inability to see either the sun or moon for long periods, most ships that plied the sea docked for the winter.
Paul, sensing that those operating the ship wanted to continue the voyage during a notoriously dangerous time of the year, warns them not to leave port (Acts 27:9 - 10). His warnings go unheeded and the ship leaves port, hoping to reach the far western side of Crete and the harbor of Phoenix.
Paul's ship never makes it to Phoenix. Strong winds and a stormy sea out of the North and North-East blow the vessel away from Crete. Unable to control the ship she is allowed to go wherever the wind takes her.
And when the ship was caught in the storm, and we were not able to bring her head into the wind, we let her go and were driven along (Acts 27:15).
It is only after wandering the sea aimlessly for two weeks that the ship finally runs aground near the island of Malta. The vessel is very soon abandoned. All those on the ship make it safely to the island, in fulfillment of what God told Paul (Acts 27:22 - 25).