In the Iliad (XI 632-637), Homer mentions the cup in which Nestor, the most aged of warriors of the Trojan War, drinks his wine. The poet describes how it was made, with golden studs and four handles, each decorated with a pigeon bending to drink from the wine in it. More significantly, he adds that when it is filled with wine, of all the warriors, "only Nestor, old as he was, could pick it up with ease from the table". In this comparison, the elderly Nestor is ranked on par with the fiercest of the young knights in the narrative: Achilles, for whom Homer uses similar expressions, not for his cup (XVI 225-8), but instead, for his horses (X 402-4), his spear (XIX 389), or for the handle that shuts the gate of the wooden fence in his camp (XXIV 455-456).
The word δέπας which the poet uses for the cup of Nestor, is also of interest. This very archaic noun is identified in a Mycenaean tablet with an ideogram, which depicts a four-handled canister, just as the cup is described in the Iliad. Subsequent poets in the antiquity used this word as a general metaphor for a "vessel", as they did for the same purpose using the names of several other kind of vases (skyphos, kantharos, gaulos etc.). From the use of the word in this manner, we can surmise that for the Greeks there was some mystic analogy springing from the Dionysian cult, which connected wine cups and ships, as well as their content, the wine, with the sea. Perhaps, this is the reason why Homer often refers to the sea as being "wine-dark". Another fascinating detail in the same scene, where the cup is mentioned, is the wine that Hekamede, Nestor's captive, uses to prepare the potent porridge, which the old King shares with his comrades. It is called "wine of Pramnos", which was the renown wine produced in ancient Icaria! What other cup, therefore, than Nestor's cup would be better, for symbolic reasons, to become the award for a sailing race that starts and ends in the island of Icaria, with elderly competitors, but still "evandroi" in body and spirit?
Two different ancient cups were excavated and have been associated with the mythical cup of Nestor. The oldest and one of the greatest artifacts of the period, dating from 1600 BC, was discovered in 1876 by Heinrich Schliemann at Mycenae, now on display at the National Archeological Museum of Athens. Just as the one which Homer describes, it is made of gold and its handles bear birds dipping to drink from its content. It is much older than the period the Trojan War took place, it has only two handles instead of four, and the birds are falcons not pigeons. Nonetheless, Schliemann quickly identified it as the mythical cup and since then the archeologists refer to it as "the golden cup of Nestor".
The second ancient vessel that is also known as "Nestor's cup" is made of clay rather than gold. It is a vase in the shape of a Rhodian "kotylos" which was found in 1954 at an excavation in the ancient Pithekoussai (the island of Ischia, Italy). It is dated approximately from the 2nd half of the 8th century BC and it is on display at the local archeological museum. The reason why this vase is referred to as "Nestor's cup" is not for its likeness to Homer's description, but for an inscription in three separate lines written on it. The short text states: "[I am?] Nestor's cup, good to drink from. Whoever drinks from this cup, him straightaway the desire of beautiful-crowned Aphrodite will seize".