If during Sukkot a person wishes to drink wine, and he does not eat anything with the wine, must he drink the wine in the Sukka? And if drinking wine indeed does require a Sukka, would one recite the Beracha of "Le’sheb Ba’sukka" in such a case?
This question also affects the recitation of Habdala on Mosa’eh Shabbat and Mosa’eh Yom Tob during Sukkot. As opposed to Kiddush, which is recited as the introduction to a meal, and therefore must certainly take place in a Sukka, Habdala consists of only wine, and does not include any food. The question thus arises as to whether one must recite Habdala in the Sukka, and, if so, whether he recites the Beracha of "Le’sheb Ba’sukka" before drinking the wine.
This issue is subject to debate among the Rishonim (Medieval Halachic scholars). The Ritba (Rabbi Yom Tob of Seville, Spain, 1250-1330) was of the opinion that wine requires a Sukka, with a Beracha, whereas the Meiri (Rabbi Menahem Meiri, 1249-1315) held that one may drink wine outside the Sukka.
Both views can be supported from the Talmud. The Mishna in Masechet Sukka (25a) states, "Ochelin Ve’shotin Arai Hutz La’sukka" – "One may eat and drink temporarily outside the Sukka." This means that the obligation of Sukka applies only to established meals; quick snacks, however, do not require a Sukka. In presenting this Halacha, the Mishna speaks of both eating and drinking, indicating that there is a situation where drinking can constitute an established "meal" of sorts. Presumably, this is possible only with regard to wine, the most significant and important beverage. This Mishna might therefore provide proof for the Ritba’s position, that drinking a substantial quantity of wine is deemed significant enough to require a Sukka.
On the other hand, the Gemara in Masechet Berachot (35) raises the question of why we do not recite Birkat Ha’mazon after drinking wine. Since wine has the quality of "Masbi’a," meaning, it provides satiation, the Gemara wondered why there is no obligation to recite Birkat Ha’mazon after drinking wine, just as there is after one eats a meal. The Gemara answered that people do not normally establish a meal over wine. Wine is drunk as an occasional drink, but not as a formal, established meal. The Gemara adds that even if there are some people who indeed make established "meals" with only wine, they comprise a small minority, which will not affect the formal Halachic status of wine. In light of the Gemara’s conclusion, it would appear that drinking wine is not deemed significant enough to require a Sukka, in accordance with Meiri’s position.
As far as the final Halacha is concerned, the Shulhan Aruch (Orah Haim 639:2) explicitly rules that one may drink all beverages – including wine – outside the Sukka. However, given the position of the Ritba who required drinking wine in a Sukka, it is certainly preferable to make a point of drinking wine specifically in the Sukka, without reciting a Beracha. What more, the Shulhan Aruch himself writes that it is laudatory to avoid eating and drinking anything – even water – outside the Sukka. Therefore, although wine may be drunk outside the Sukka according to the strict Halacha, it is preferable to drink wine in the Sukka.
Summary: Strictly speaking, one may drink wine outside the Sukka during Sukkot. Preferably, however, one should do so inside the Sukka. In fact, it is an admirable practice to ensure not to eat or drink anything outside the Sukka throughout the holiday of Sukkot.
