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Paul was converted around A.D. 35. The fourteen years he mentions are probably calculated from the time of his conversion.

This trip to Jerusalem was not his first. Most likely, he made his first trip to Jerusalem around A.D. 38,and other trips to Jerusalem in approximately A.D. 44, A.D. 49/50, A.D. 52, and A.D. 57. Paul even visited Jerusalem on other special occasions as well.

Barnabas and Titus were two of Paul’s close friends, a faithful believer and church leader serving on the island of Crete.

Galatians 2:1
Then after fourteen years, I went up again to Jerusalem, this time with Barnabas. I took Titus along also.