Acts 20:6

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Acts 20:6 And we sailed from Philippi with the days of unleavened bread.

They “sailed with the days of unleavened bread.” This is similar to saying “The flowers bloomed with the spring days.” Or “We set out with the first days of spring.” The Greek preposition “μετὰ” when used with a verb of motion means “into the middle of”, “during”, “along with”.

And we came to them into Troas, up to five days,

The problem with this interpretation is that the voyage does not take five days. It only takes two days or three at most. If conditions were so bad that it took five, then the hazard of the trip would surely have been mentioned. For it would take a mighty wind storm to make the voyage last that long. The typical voyage only takes two days, and not just because Acts 16:11 indicates this, but because a maritime study of passage from Philippi to Troas will show this. http://www.cruiserswiki.org/wiki/Aeg...ents_.26_Tides

where we completed the seven days [of Unleavened Bread]. 7 And on the first of the Sabbaths

The seventh day of the feast was an Annual Sabbath, which is followed immediately by the first of the Sabbaths that year. This is an unusual circumstance when the seven days of the feast are all used up before the first of the Sabbaths. Usually, the first of the Sabbaths falls during days 2 to 7 of the feast. It is so noted by Luke that they completed the feast before the first of the Sabbaths. This circumstance shows that the seventh day of the feast fell onto Friday that year, and the first day of the feast fell onto the weekly Sabbath before.

As I said before the word σαββάτων means “Sabbaths”, it is plural in Greek. The first Sabbath day after Passover is the only one that is given the name of "first of seven Sabbaths" which are counted between Passover and the feast of Shavuot ( Lev. 23:15).

when we were gathered together to break bread, Paul was talking to them, intending to depart the next day, and he prolonged his message until midnight.
 

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It doesn't say that they sailed for 5 days - it says that at [some time after Unleavened Bread] they sailed from Philippi [and] 5 days later they met the others who were waiting for them at Troas, where they all stayed for a week.

We cannot assume that they got on the boat and didn't get off until 5 days later - what we do know is that they sailed at some point after the Feast, not necessarily the day immediately after it. :)

The Motza'ei Sabbath may not necessarily have been on arrival - it may have been during the 7 days they spent together.

Luke is terrible with his timings!
 
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