“For I am now ready to be offered, and the time of my departure is at hand. I have fought a good fight, I have finished my course, I have kept the faith: Henceforth there is laid up for me a crown of righteousness, which the Lord, the righteous judge, shall give me at that day: and not to me only, but unto all them also that love His appearing” (II Timothy 4:6-8).
Approximately two years after being delivered into the hands of Roman authorities things had apparently gone well for the apostle, therefore he anticipated his soon release from prison. Thus he writes to the church at Philippi: “For I know that this [their prayer for his release] shall turn to my salvation [deliverance from prison]” (Phil. 1:9).
We believe that Paul did in fact enjoy a short period of freedom which enabled him to continue his apostolic journeys. We know, for example, that according to the Acts record the apostle never visited Crete on any of his previous apostolic journeys. Paul did sail around the island on his way to Rome as a prisoner, but it was not until his release from his first Roman imprisonment that he actually visited Crete. The apostle’s brief stay on the island was long enough to see that the churches there were in a state of chaos (Titus 1:10-16). Consequently, Paul leaves Titus behind, his companion in travel, “to set in order the things that were wanting” (Titus 1:5).
Probably from Crete Paul made his way to Corinth where he writes to Titus to inform him that he planned to winter in Nicopolis (Titus 3:12). It could well be that the apostle was apprehended at Nicopolis and taken again to Rome for preaching Christ. This time however, the sentence would go against him. So without hesitation he writes to Timothy, since it was nearing winter, to bring his cloak and also the Parchments (II Tim. 4:13). source