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The return to we indicates Luke’s presence with Paul throughout his imprisonment and hearings (21:17-18; 27:1). Paul and his companions, under the guard of Julius and, presumably, the hundred soldiers under a centurion, set off on a coastal ship. Such ships sailed close to the coast from port to port and were unsuitable for a straight voyage to Rome on the open sea. They obviously hoped to find at one of the ports a seagoing ship that would carry them to Rome. After port-hopping from Caesarea to Myra, they find a large grain ship that plied the route from Alexandria to Rome with the Egyptian wheat that kept Rome alive (vv.1-6).
The difficulty in sailing from Myra in Asia to Fair Havens in Crete (vv.7-8) was due to the onset of winter. From mid-September to mid-November the Mediterranean becomes dangerous as the Sahara high pressure mass moves from its usual summer position over the Mediterranean to its winter position over Africa, allowing the storms from the North Atlantic and the Russian steppes to ravage the Mediterranean. Luke notes that the fast of the Day of Atonement (October 5, in a.d. 59, cf. Bruce, 455) was already past; therefore they were into the danger season. After mid-November, there was no sailing throughout the winter.
Paul apparently receives discernment about the voyage, but who will listen to a prisoner (vv.10-11)? Instead, lulled by a fair day, they try to sail from Fair Havens, which provided no shelter from the winter storms, to Phoenix, which had a good winter harbor (vv.12-13).