Meanings according to Rider-Waite:
ASTROLOGICAL SIGNIFICANCE: Saturn/Moon as a symbol of sorrowful farewell.
EIGHT OF CUPS The Eight of Cups is one of the three "breakthrough" cards, signifying a sorrowful farewell (along with the Chariot, which means the joyful "departure of the hero" onto the battlefield, and the Six of Swords, symbolising a journey into the unknown, towards new shores). It shows that we must leave our familiar surroundings, part with people or things to which our "hearts have grown attached," and set off on a long journey into an unknown future. In any case, it bears witness that we have not been driven out — we ourselves, of our own will, have decided to leave (although it may also be that we had no other choice). The "heaviness of parting" lies in two aspects: we must abandon what is dear to us, and we do not know what awaits us.
From the book: Hajo Banzhaf. THE TAROT HANDBOOK. Translated from German by E. Kolesov. Publisher: Centre for Astrological Research, 1999.
EIGHT OF CUPS Indolence The first decan of Pisces, from 19 to 28 (29) February. Astrological equivalents: Virgo, Scorpio. The first decan of Pisces symbolises an inner need for the highest and an emergence into mystical spiritual experiences, into the inspiration that is born when a person surrenders his will to the unknown. It is a quiet immersion into the waves of life and a fateful resignation to what is happening, founded on the understanding that the life process as a whole is wiser than the pretensions of any single human being. This decan is ruled by the planet of predestination, Saturn (in the modern system — Neptune, which inclines one to contemplation). Saturn emphasises the departure from traditional emotional canons towards one's own sensory criteria, which seals the final emotional break with the former conception of the world. People of this decan are more inclined to a subjective perception of events, and they are prone to a fascination with the unreal and a romantic preoccupation with things that do not exist in objective reality — but which, in all likelihood, lie at the bottom of our collective unconscious. This decan symbolises a strictly individual mystical path of the human being, and therefore its representatives are sometimes distinguished by imperturbability, withdrawnness, an inclination towards solitude and a sense of rejection, as well as a certain gloominess. The TAROT card depicts a man who has left behind all his past experiences and inner attainments — eight filled CUPS — and, with a wanderer's staff, walks towards the dark mountains of the unknown. Above him is the Sun in conjunction with the Moon: the new moon astrologically symbolises spiritual equilibrium and the beginning of something new, while the solar eclipse, on the contrary, signifies the dangers of the depths of life that are not illuminated by the bright light of reason. The card may also be interpreted as the discovery of new possibilities of our psyche and the paths to their rational comprehension. At the level of the EIGHT OF CUPS, emotion, already fully conscious and having taken on sufficiently concrete forms, undergoes a reconciliation with logic, with reason. Therefore the card indicates either a harmonising of reason and feelings, or their disharmony. On the level of love relationships, the EIGHT OF CUPS may bear witness to difficulties that are overcome through patience and a tactful approach. In the sphere of human relationships, the card symbolises the mutual adjustment of two strong individualities. The positive action of the EIGHT manifests itself in the harmonious combination of desires and passions with reason. It is a situation in which love does not harm one's work, nor business relations one's love. The trap is to take the path of least resistance. Comfort.
UPRIGHT POSITION In the upright position, the card may indicate such qualities as bashfulness, modesty, restraint, shyness, great practicality, chastity, knowledge of social ritual, the ability to remain in harmony with people while maintaining distance. That is, Virgo is at work. The card may also symbolise confrontations with habit, the rejection of stagnation, inertia, or success. The lower is sacrificed in the name of the higher.
REVERSED POSITION In the reversed position, the card indicates emotions that are, as it were, absorbed. At the same time, this card may indicate sudden gifts, and rather substantial ones at that (Scorpio is at work, a sign that does not bother with trifles). It is not impossible that you yourself have ripened to the point of giving someone a gift. The EIGHT OF CUPS indicates a desire that is difficult to satisfy. The content of this card gravitates, in general, towards two words — satisfaction and stupor.