The Posuk says (Devarim 28:68):

וֶהֱשִׁיבְךָ יְ־הֹוָ־ה מִצְרַיִם בָּאֳנִיּוֹת בַּדֶּרֶךְ אֲשֶׁר אָמַרְתִּי לְךָ לֹא תֹסִיף עוֹד לִרְאֹתָהּ

And the LORD shall bring thee back into Egypt in ships, by the way whereof I said unto thee: ‘Thou shalt see it no more again.’

Why on boats?

  • Historically speaking, one of the most common forms of trade in Egypt was through ships coming down the Nile from the Mediterranean Sea. See here. – ezra Jan 15 '18 at 15:14

Ships are used for slaves and goods. It is dangerous to go on a ship, and they have a negative connotation.

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    Indeed, Rashi simply says "in ships, in captivity," and Daas Zekeinim adds that this implies that women and children will be taken captive and sold too (whereas if the non-Jews would make the captives march on foot, they'd take only adults who would be capable of surviving such a trip). – Alex Feb 16 '12 at 15:40

The Chasam Sofer answers and says it is in contradistinction to leaving Egypt when Hashem split the Sea for the Jews.

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    where does he write this? – mevaqesh May 21 '17 at 22:26

R. Yosef Kara there writes (there) that this was a particular punishment since it included those unable to walk:

אינה דומה שבייה שהשבויים מוליכים ברגל למוליכים אותה באניות, שהשבייה שמוליכים ברגל מניחין הזקן והחולה והטף והרה ויולדת יחדיו, שאינן יכולין ללכת ברגל, ומוליכין השבייה שיש בהן כח ללכת. אבל השבייה שמכניסין אותן בספינה טף ונשים בחור ובתולה הרה ויולדת הכל מכניסין בה.

Hizkuni (there) follows this explanation, as does the Da'at Z'kenim (there) as well, who writes:

באניות. ויהיו שבים טף ונשים שאם היו מוליכין אותן ברגל לא היו שבים רק הגדולים היכולים ללכת ברגל

In boats: And they would transport children and women. For had they transported them by foot, they would have just taken the adults who could travel by foot.

This is stated by the Paneah Raza (14th cent.) (there) as well.

R. Yitshak Karo writes a different explanation in Tol'dot Yitshak (there). The verse is contrasting the heights to which Israel rose, with the depths to which they would sink. They first crossed miraculously on dry land to freedom, but they would ultimately return in boats in captivity, without miracles.

Alternatively, HaKtav V'HaKabbalah (there) suggests that it means going in mourning (as in Lamentations 2:5).

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Rav Kanievsky answers it says in Medrash Eicha(פ"ד סי' כ) That the Jews had a treaty with Egypt's King Pharaoh the Limp and an enemy attacked the Jews they called on Egypt an the Egyptians were coming to save them. Hashem caused the bodies of the Egyptians who had drowned at the splitting of the sea to surface one asked the other who are these people they answered theses are our ancestors who the Jews drowned and the turned around and left.This is why the Boats are mentioned as this was the Payback for our sins.

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    Which Rav Kanievsky? Where does he write this? – mevaqesh May 21 '17 at 22:26

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