Sailing in New Testament times was a dangerous proposition. In 2 Corinthians 11:5, Paul says he has been shipwrecked three times. He was shipwrecked at least one other time as described in Acts 27 and 28.
Ships were only capable of sailing with the wind. In the Mediterranean Sea, the wind generally was from the south in the summer and from the north in the winter. So the great grain ships that supplied Rome left in the spring to go to Africa and returned as soon as possible. During the winter months, winds were so unpredictable that it was dangerous after mid-September, and impossible after early November. Visit https://eyewitnessbible.org/one-hit-wonders/ for the full synopsis, study materials, and more!

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