On the first night of the festival of Pesach the Seder ceremony is held. In a similar fashion to the festival of Purim which takes place exactly a month before, wine plays an important role in the proceedings. However, whereas in the case of Purim wine is used to numb the senses, on Pesach it is used to heighten our awareness of the miraculous events that took place and to symbolize them.
The First Cup
The first cup of wine is used to recite Kiddush, that is, the sanctification of the festive day through the blessing and drinking of wine. In the Kiddush, the Jewish people thank G-d for making them holy as His chosen people and thereby enabling them to make the festive days holy.
The Second Cup
This cup is drunk after the fulfillment of the part of the Seder ceremony called Maggid. In Maggid, the participants of the Seder fulfill the commandment to relate the story of the exodus from Egypt. Psalms of thanksgiving are recited, ending in a request for the final redemption. After the blessing over G-d redeeming Israel the cup is drunk, leaning to one’s left side (it is an obligation to lean to the left while drinking the cups of wine on Seder night because this is an expression of freedom).
The Third Cup
The third cup is drunk following the recitation of Grace after Meals. This cup represents our gratitude to G-d for providing for our every need.
The Fourth Cup
The final cup is drunk after the concluding psalms of praise are recited. This section of the night focuses on the future, requesting redemption for the Jewish people and humanity at large. After the drinking of this cup the Seder is concluded.
An interesting interpretation of the reason for four cups is offered by the Sh’lah (Rabbi Yeshaya HaLevi Horovitz). He explains that the cups represent the four matriarchs, Sarah, Rebecca, Rachel and Leah. The three patriarchs, Abraham, Isaac and Jacob, and their roles in building the Jewish nation are mentioned in the Haggadah text which guides us through the Seder. The four matriarchs and their respective roles are hinted at through the four cups and their positions in the Seder. See the following link for a more extensive explanation: http://www.torah.org/learning/yomtov/pesach/5757/vol3no02.html#
The Kiddush Cup is a revered ceremonious object in Judaism and what better way is there to adorn one’s Seder than with a unique, intricate Kiddush cup. Click here to see an extensive selection of special Kiddush cups. It is the perfect way to welcome in the approaching festival and can be used afterwards throughout the year on other festivals and Sabbath days.