Paul Imprisonment

[Acts]Bribery in a judge was punishable by the Roman law, but the spirit of a slave (to use the words of Tacitus) was in all his acts, and his communing with Paul", as if he cared for either him or his message, simply added hypocrisy to meanness. Publius (or Gaius) Cornelius Tacitus (AD 56 – AD 117) was a senator and a historian of the Roman Empire. While Tacitus' works contain much information about his world, details regarding his personal life are scarce.
The position in life of Paul's Christian visitors might beget the hope of extracting something from them for the release of their champion; but the missionary would rather lie in prison than stoop to this!
After two years in prison, what a trial to this burning missionary of Messiah, to suffer such a tedious period of inaction! How mysterious it would seem! But this repose would be medicine to his spirit; he would not, and could not, be entirely inactive, so long as he was able by pen and message to communicate with the churches; and he would doubtless learn the salutary truth that even he was not essential to his Master's cause. That Luke wrote his Gospel during this period, under the missionary’s superintendence, is the not unlikely conjecture of able critics.
Porcius Festus was procurator of Judea from about AD 58 to 62, succeeding Antonius Felix. His exact time in office is not known. Luke claims he arranged Paul's audience with Agrippa; but the Lukan chronology cannot be coordinated with events mentioned by Josephus.
The plan of Felix, therefore, in suppressing the enmity of the Jews, and conciliating their favor by injustice to Paul, did not succeed; and is one of those instances, so numerous in the world, where a man gains nothing by wickedness. He sought money from Paul by iniquity, and failed; he sought by injustice to obtain the favor of the Jews, and failed in that also. And the inference from the whole transaction is, that "honesty is the best policy," and that man in any office should pursue a course of firm, and constant, and undeviating integrity.He died a few years after this [Josephus, Antiquities, 20.8.9-9.1. Festus' sudden death (62 CE) left Judea temporarily without a Roman governor. In the interim before the arrival of his successor, Lucceius Albinus, the Sadducean high priest [Hanan II] arranged the execution of Y’Shua's brother James along with others on charges of Torah violations.
Paul may have spent as much as 25% of his time as a missionary in prison. We know of his brief lock-up in Philippi (late 49 A.D.), two years' incarceration in Caesarea 58 A.D., and at least another two in Rome (60-62 A.D. Yet Paul says he experienced "far more imprisonments" than his opponents. To understand Paul, we need to understand where he spent so much time. Paul is back in a Roman prison in the city of Rome in 67 A.D. Paul stays in jail until he is put to death by the Romans around May or June 68 A.D.
During his ministry the missionary Paul spends roughly 5 1/2 to 6 years as a prisoner or in prison.
Roman imprisonment was preceded by being stripped naked and then flogged, a humiliating, painful, and bloody ordeal. The bleeding wounds went untreated; prisoners sat in painful leg or wrist chains. Mutilated, blood-stained clothing was not replaced, even in the cold of winter. In his final imprisonment, Paul asked for a cloak, presumably because of the cold.
Most cells were dark, especially the inner cells of a prison, like the one Paul and Silas inhabited in Philippi. Unbearable cold, lack of water, cramped quarters, and sickening stench from few toilets made sleeping difficult and waking hours miserable.
Male and female prisoners were sometimes incarcerated together, which led to sexual immorality and abuse. Prison food, when available, was poor. Most prisoners had to provide their own food from outside sources. When Paul was in prison in Caesarea, Felix, the procurator, gave orders to the centurion that "none of his friends should be prevented from attending to his needs."
Because of the miserable conditions, many prisoners begged for a speedy death. Others simply committed suicide.
All of this could be mitigated to some extent if the prisoner was important or paid a bribe (as Governor Felix hoped to receive from Paul in Caesarea).
A prominent individual, or one expected to be released, might be kept under house arrest if he or she could afford the rent. In Rome, where housing prisoners was excessively expensive, Paul was given the privilege of house arrest, and he paid the rent himself (exactly how, we don't know). He probably lived in a third-floor apartment; first floors were used for shops, and the second floor was expensive.
In his final imprisonment in Rome, though, Paul's life came to an end in the woeful conditions of a Roman prison (John McRay, "Paul and His Times," Christian History, No 47).