Rashi #1 (citing R. Moshe ha'Darshan), Ramban and R. Bachye #1 (on Pasuk 2): To teach us Hashem's kindness - since, even though He decreed that He would move them around in the desert, we should not think that He moved them incessantly from place to place without respite throughout the forty years. ¹ We see here that they only made forty-two journeys. Deduct fourteen that they made during the first year ² - before the decree was issued - and eight, which occurred after the death of Aharon in the fortieth year, ³ after the decree had been rescinded, and it transpires that, during the thirty-eight years ⁴ that the decree was in place, they only traveled twenty journeys.

Rashi #2 and R. Bachye #2 (on Pasuk 2 - both citing Midrash Tanchuma): It can be compared to a king who took his sick son on a long journey to obtain a cure, and who, on the return journey, began to recall the stops that they made on the way out - 'Here we slept!' Here we suffered from the cold!' Here you had a head-ache!' ⁵

Ramban #1 and R. Bachye #3 (in his introduction to the Parshah, both citing Moreh Nevuchim): To negate the notion that Yisrael survived forty years in the desert by living in the outskirts close to inhabited country, ⁶ within range of grazing-grounds for their cattle or in areas where vegetation and plants were available to provide them with food and many springs to provide them with water. Therefore the Torah describes their itinerary, that we should realize that they traveled far from inhabited country, where no food and no water was available, ⁷ places where, under normal circumstances, nobody could possibly survive. ⁸

Ramban #2: It was a Divine Command to write down all the places that they passed, for the above reasons - Refer to answers 1 & 3 - or for some unknown reason that Hashem did not reveal.

R. Bachye #4 (citing the Yerushalmi): To teach us that Hashem led them in the desert according to the way they thought about Hakadosh-Baruch-Hu - when their thoughts were good, He led them with Midas Rachamim - ?Vayachnu be?Har Shafer? ⁹ and ?Vayachann be?Miskah? ¹⁰ - to protect them; and when they were bad, He led them with Midas ha?Din - ?Vayachanu ba?Charadah, ¹¹ be?Dafkah? ¹² and ?be?Marah? ¹³ - to punish them. ¹⁴

Rashbam: The Torah repeats their itinerary, to teach us the names of the places where they encamped.

Seforno: It is to teach us the merits of Yisrael, how they followed Hashem in the desert, a place where nothing grows, in a way that rendered them worthy to enter Eretz Yisrael.

Targum Yonasan: To make us aware of the miracles ¹⁵ that Hashem performed with Yisrael.

Malbim (on Pasuk 5): The Masa'os correspond to the letters of Hashem's forty-two-letter name, and they hint at what will be before the final redemption. ¹⁶

Oznayim la'Torah: In order to rid Yisrael of a lifetime of Avodah Zarah and sin - and particularly bearing in mind that they were accompanied by the Eirev Rav - and to train them in the performance of Mitzvos, Hashem led them for forty years in a miraculous, under the leadersh ip of 'the man of G-d', who taught them the Torah, and in a way where they witnessed firsthand the wonders and miracles that Hashem performed with them - the reward for doing good - Keri'as Yam-Suf, Miriam's well, the Manna, Matan Torah, the Ananei Kavod ... on the one hand; and the punishment - that came swiftly, on the other - "Is Hashem in our midst?" -'And Amalek came'; They complained - 'A Divine fire burnt among them"; "They desired" - They were buried in Kivros ha'Ta'avah; "They brought out a bad report of the land" - '"And they died by a plague from before Hashem". This, together with Moshe's repetition of Seifer Devarim woul prepare them for a life of Torah and Mitzvos when they arrived in Eretz Cana'an. ¹⁷

R. Bachye: Refer to 33:6:1:2*.