Eating & Drinking on Holidays

"To sanctify it" - with a blessing. From here, they said: "We sanctify over wine upon its entry."

This is only for sanctification of the day, whence is it that kiddush should be performed at night? We learn it from "And you shall observe the Sabbath" (Ex. 31:14).
This is only for Shabbat, whence is it that we do kiddush for holidays? We learn it from "These are the festivals of the Lord, which you shall call in their times" (Lev. 23:4).

[If one needs to choose between] The honor of the day and the honor of the night [for Shabbat]: the honor of the day takes precedence over the honor of the night.

If one only has one cup [of wine], the holiness of the day (which takes place at night) takes precedence over the honor of the day and honor of the night [of Shabbat].

Both nights of Shabbat and holidays have sanctification of the day over a cup [of wine] and sanctification of the day in the Grace After Meals.

New moons and intermediary days of holidays have sanctification of the day in the Grace After Meals, but not a sanctification of the day over a cup [of wine].

It is taught:

Rabbi Eliezer says: "A person has either to eat and drink on a festival, or sitting and studying."

Rabbi Yehoshua says: "Divide it: Half to God and half to yourselves."

Rabbi Yoḥanan said: "And both of them derived their opinions from one duo of scriptural verses relating to this issue: one verse states: 'It shall be a solemn assembly for the Lord, your God' (Deuteronomy 16:8), and one verse states: 'It shall be a solemn assembly for you' (Numbers 29:35).

How is this?

Rabbi Eliezer opines either entirely for God, or entirely for you; and Rabbi Yehoshua opines Split it: half of it for God and half of it for you."

It was taught:

On a Festival, one is slow to arrive and one is quick to leave;

on Yom Kippur, one is quick to arrive and slow to leave;

and on Shabbat, one is quick to arrive, and quick to leave.

It was taught:

Rabbi Yehudah ben Beteira says: "When the Temple is standing, rejoicing is only through meat, as it is stated: 'And you shall sacrifice peace-offerings and you shall eat there and you shall rejoice before the Lord your God' (Deuteronomy 27:7). And now that the Temple is not standing rejoicing is only by wine, as it is stated: 'And wine that gladdens the heart of man' (Psalms 104:15)."

The Sages taught:

A man is obligated to gladden his children and the members of his household on a Festival, as it is stated: “And you shall rejoice on your Festival, you, and your son, and your daughter, and your manservant, and your maidservant, and the Levite, and the stranger, and the fatherless, and the widow that are within your gates” (Deuteronomy 16:14).

With what does one make them rejoice? With wine.

Rabbi Yehudah says: "Men with what is fit for them and women with what is fit for them."

Men with what is fit for them - with wine.

And women, with what?

Rav Yosef taught: "In Persia, with colored clothes, and, in the land of Israel, with pressed linen clothes."

In the same way that there is an obligation to honor the Sabbath and to delight in it, so too [is it with] the holidays. As it is stated (Isaiah 58:13) "to sanctify the honored Lord"; and it is stated about all of the holidays (Leviticus 23:7), "a time of holiness." And we have already explained [this] honoring and delighting in the laws of the Shabbat. It is therefore fit for a person to refrain from having a meal on the eve of holidays from the time of the afternoon prayer, like on the eve of Shabbat. As this thing is part of [its] honor. And anyone who disgraces the festivals is as if he was associated with idolatry.

...And one is obligated to be joyful and of a good heart on them—he, his children, his wife, the members of his household and all who accompany him. As it is stated (Deuteronomy 16:14), "And you shall rejoice in your holiday, etc." Even though the joy that is mentioned here is [referring to] peace offerings—as we explain in the Laws of the Festival Offering—included in that joy is for him, his children and the members of his household to rejoice—everyone according to what is fit for him.

The children, for example, should be given parched grain, nuts, and sweetmeats; the womenfolk should be presented with pretty clothes and trinkets according to one's means; the menfolk should eat meat and drink wine, for there is no real rejoicing without the use of meat and wine. ...

Even though eating and drinking are included in the positive commandment (of joy on the holiday), one should not eat and drink the whole entire day. Rather this is the appropriate measure: All of the people get up early in the morning [to go] to the synagogues and study halls to pray, and to read in the Torah about the topic of the day. [Then] they go back home, eat, and go to the study hall, [where they] read and study until midday. And after midday, they pray the afternoon prayers and return to their homes to eat and drink for the rest of the day, until the night.

And what Rabbi Yaakov ben Asher wrote in his Four Columns that one needs to honor and to enjoy festivals just as we honor and enjoy Shabbat, such has Maimonides written in chapter 6: "In the same way that there is an obligation to honor the Sabbath and to delight in it, so too [is it with] the holidays, as it is stated 'to sanctify the honored Lord' (Isaiah 58:13), and it is stated about all of the holidays, 'a time of holiness' (Leviticus 23:7). ... It is therefore fit for a person to refrain from having a meal on the eve of holidays from the time of the afternoon prayer, like on the eve of Shabbat, since this matter is included in honoring." And there are those who say that we need to eat three meals on holidays, and such has Maimonides written in chapter 30 of Shabbat Laws, but his words are not convincing.

We learn in the Talmud (Berakhot 39b): "Rabbi Abba said: 'A person is obligated to break bread over two loaves on Shabbat.' What is the reason? 'They gathered double the amount of food' (Ex. 16:22)."
And Rabbi Isaac Alfasi wrote "and the rabbis explained that holidays also require breaking bread over two loaves, just as with Shabbat, since the primary obligation of Shabbat was since the man did not fall on Shabbat, rather it fell in pairs on Fridays, and holidays would be the same in that the man would not fall on holidays, rather they would fall on holiday eves in pairs, just as they would for Shabbat eves. Therefore, we need to break bread on holidays over two complete loaves of bread, just as we are obligated on Shabbat" (Pesahim, ch. 10).

And, similarly, did Maimonides write (Shabbat laws, ch. 30). And he wrote that we also need to establish every meal upon wine, just as with Shabbat.

The anonymous author of the Everything-In-It (KolBo) wrote that there are those who have written that the third meal on holidays is when people eat an additional dish, aside from the first, even though one hasn't interrupted with the Grace After Meals. And people were only stringent to do so on Shabbat.

It is an obligation for a man to be happy and in good spirits on the holiday - him, his wife, his kids, and all who are with him.

How should he make them happy? He should give the children nuts and the women new clothes and jewelry according to his finances.

One should eat, drink, and be happy on the holiday.

One should not overindulge in meat, wine, laughter, or frivolity, because laughter and frivolity are not happiness but debauchery and foolishness.

We were not commanded to engage in debauchery and frivolity but only happiness that involves worshipping the Creator.

It is a mitzvah to spend half the time of a holiday in the study house and half of the time eating and drinking.

One should not skimp on holiday expenses; it must be honored and enjoyed like Shabbat.

It is an obligation to break bread upon two loaves and to establish every meal upon wine.

One eats and drinks...even if one denies oneself on account of repentance throughout the year without eating meat nor drinking wine, one is obligated to eat and drink these on Shabbats, holidays, Hanukah, and Purim.