Question: Why do we sit in a sukkah? Is one allowed to travel during Sukkos to a place where no sukkah is available?
Answer: The Torah tells us why to sit – or, rather, dwell – in a sukkah: “Lema’an yed’u doroteichem ki vasukkot hoshavti et Bnei Yisrael be’hotzi’i otam me’eretz Mitzrayim; ani Hashem Elokeichem – So that your [future] generations will know that I made the Children of Israel dwell in booths when I took them out of the land of Egypt; I am the L-rd your G-d” (Vayikra 23:43).
By observing this mitzvah, we remember all the wonders that G-d wrought for our ancestors when He delivered them from Egypt.
The Rambam notes in his Moreh Nevuchim (III:43) that Sukkot comes after a season of intense labor in the fields when people are free from pressing agricultural chores and are able to rest. At that time, we remind ourselves of more difficult days and that G-d provided for us in the desert. Thus, we dwell in booths like nomads in the desert, away from the elegant homes and fertile land which we now enjoy thanks to “the kindness of G-d and because of His promises to our forefathers, Abraham, Isaac, and Jacob.” This mitzvah teaches us a lesson in humility and the need to thank G-d.
The Torah instructs us to dwell in a sukkah for seven days, but in exile we traditionally sit in one for eight days. However, because of sefeika d’yoma (we don’t know if the last day is Sukkot or Shemini Atzeret), we do not say the blessing of “leishev ba’sukkah” the last day (see Orach Chayim 668:1; also Ba’er Heitev, regarding various minhagim on dwelling in a sukkah on Shemini Atzeret).
On the first night, though, we must eat in a sukkah. The Rema (op. cit. 639:5) rules that we have to make Kiddush in a sukkah and eat a kezayit (an olive size’s worth) of food. The Mishnah Berurah (ad loc.) discusses in great detail the various opinions regarding how long to wait if it’s raining on the first night of Sukkot.
Generally speaking, though, we abide by the rule expressed by Raba (Sukkah 26a) that “mitz’ta’er patur min ha’Sukkah,” one who is uncomfortable sitting in a sukkah (because of conditions inside it) is exempt from the obligation to dwell in a sukkah.
The Talmud (ibid.) states that those who travel during the day need not sit in a sukkah at that time but must do so at night. Those who travel at night are exempt at night but not during the day. Those who travel during the day as well as at night (i.e., they are on a long journey) are exempt all day and all night long. People traveling for a mitzvah are also exempt all day and all night (even if they are only traveling during the day – see Rashi ad loc.).
Rashi (ibid. 26a) writes that these rules are based on the Gemara’s explanation (ibid. 28b) of Leviticus 23:42: “Ba’sukkot teshvu shiv’at yamim – In booths shall you dwell for seven days.” How should you dwell? “K’ein taduru,” says the Gemara. “In the manner in which your ordinarily dwell.” Therefore, since people do not refrain from traveling all year round, there is no reason to refrain from traveling on Sukkot.
Nonetheless, since the mitzvah of sukkah only comes around once a year, we should be anxious and fastidious to fulfill it, just like we are for all the other mitzvot of the chag (lulav, etrog, etc.). In this spirit, in recent years people who travel have taken along portable “pop-up sukkot.” Of course, anyone who erects these sukkot should make sure to do so only in areas where it is allowed, or they have obtained permission, to do so.
It is our fervent prayer that Hashem grant us a Sukkot during which we bask in His glory and He rewards our observance with the geulah sheleima speedily in our days.