Why does the Torah write "He'alos he'Anan" and not 'Alos he'Anan'?
Rashi: Because "He'alos he'Anan" means 'the Cloud departed', whereas 'Alos' would have meant 'the Cloud rose'.
What does the Torah mean when it writes "ve'Acharei-Chein Yis'u ... "?
Seforno: It means that when the Cloud lifted, Yisrasel would travel in the direction that the Cloud indicated.
Oznayim la'Torah: The Torah writes "ve'Acharei-Chein Yis'u" and not 've'Achar-Chein', because 've'Achar-chein' implies that they traveled immediately, whereas in fact, they only traveled after the Kohaniam had blown the trumpets and Moshe had given the order to travel. 1
Why does the Torah go into such intricate detail regarding their travels in the desert?
Ramban and Seforno: In praise of Yisrael, who followed instructions without complaining, even when the conditions were unfavorable. Sometimes they encamped in a location that was empty and where hyenas howled; 1 Sometimes they would remain in such a place for a long period of time without searching for better camping -ground. 2 Sometimes the location was ideal for them both personally and as regards grazing for their cattle; 3 nevertheless when the Cloud moved on they did not complain; 4 Sometimes they stayed in a location for just one night, leaving them insufficient time even to unpack 5 before they moved on; 6 and sometimes they had barely managed to get organized when they broke camp, or they remained a long time in one location, and just as they had begun to settle down, they suddenly had to move. 7
Oznayim la'Torah: Sometimes the Cloud remained in one location for a long period of time which was so unpleasant that a day seemed like a year - yet, when the Cloud remained, they followed suite. 8 Sometimes, the Cloud remained in a pleasant location for what "seemed like a few days" 9 - yet when the Cloud traveled, they broke camp and traveled too. 10 Sometimes, it was only overnight, leaving them barely enough time to rest from the previous journeying - yet when the Cloud traveled, they broke camp and traveled too. 11 Sometimes the Cloud remained only a day and a night and rose before daybreak 12 - yet they rose in the night to be ready to leave at the crack of dawn. 13
Seforno: Pasuk 17.
Seforno: Pasuk 19.
Or because they were travel-weary (Ramban).
Seforno: Pasuk 20.
Seforno: Pasuk 21.
Or because they had just unpacked and were immediately required to re-pack - "Yomam va'Laylah" (Ramban]):
Seforno: Pasuk 22.
"u've'Ha'arich he'Anan ... ve'Lo Yisa'u ... Veshamru es Mishmeres Hashem ... " - Pasuk 19.
See Vayeitzei Bereishis, 29:20.
"ve'Yesh ,,, Yamim Mispar ... ve'al-Pi hashem Yis'u" - Pasuk 20.
"me'Erev ad Boker ... Vena'aleh he'Anan ba'Boker Venasa'u" - Pasuk 21.
See Oznayim la'Torah.