Acts 20:3
The “three months” appear to have been the winter months of A.D. 56-57. Paul probably spent most of this time in Corinth where Gaius (Titius Justus?) was his host (Rom_16:23; cf. Act_18:7). There he wrote the Book of Romans as he anticipated visiting Rome. From Rome he planned to move farther west into Spain (Rom_15:24). During his time in Macedonia and Achaia Paul was also busy collecting the gift for the poor saints in Jerusalem (Rom_15:26). He evidently planned to travel on a ship from Cenchrea to Caesarea and Jerusalem to celebrate one of the spring Jewish feasts there (Act_20:6; Act_20:16). However when he learned of the Jews’ plot to kill him on the way, he changed his plans and decided to go to Jerusalem by way of Macedonia. Constable
“Often from foreign ports Jewish pilgrim ships left for Syria to take pilgrims to the Passover. Paul must have intended to sail on such a ship. On such a ship it would have been the easiest thing in the world for the fanatical Jews to arrange that Paul should disappear overboard and never be heard of again.” [Note: Barclay, p. 161.]