Either Artemas or Tychicus presumably will take Titus’ place in Crete, and when either one arrives, Titus is instructed to join Paul at Nicopolis, since Paul plans to spend the winter there. There marks Paul as not being in Nicopolis when he was writing this letter; but wherever he was, it is certain that he was not in prison, since he was free to travel. There is nothing known about Artemas, since he is mentioned only here; Tychicus, however, is mentioned in 2 Tim 4.12 (see also Acts 20.4; Col 4.7; Eph 6.21), and it is safe to assume that these refer to the same person. As to Nicopolis (literally “city of victory”), there are at least seven cities at that time bearing this name, but it is likely that what is meant here is the city by that name that is located in Greece, northwest of Corinth and Athens, on the shore of the Adriatic Sea. This city, we are told, was founded by the emperor Augustus to mark his victory over Mark Antony in 31 B.C. Contemporary English Version divides the first part of the verse into two sentences as follows: “I plan to send Artemas or Tychicus to you. After he arrives, please try your best to meet me at Nicopolis.” This will be a helpful model for many translators.

For do your best see 2 Tim 2.15.

Decided translates a verb that usually means “to judge,” but in this context it refers to the act of evaluating a situation and coming to a definite decision. The decision here is to stay in Nicopolis during the winter.

Winter is one of the four seasons in the nontropical parts of the world, the other three being spring, summer, and autumn. Of these four seasons, winter is the coldest. In the area where Paul lived, winter was also known for stormy weather, when the wind made it difficult to travel safely by ship. In languages where there is no word for winter, an equivalent expression may be used, as for example, “the cold season,” “when it gets cold,” or “the cold months.”

Quoted with permission from Arichea, Daniel C. and Hatton, Howard A. A Handbook on Paul’s Letter to Titus. (UBS Handbook Series). New York: UBS, 1995. For this and other handbooks for translators see here .