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What was used in that upper room was probably just an ordinary terra cotta cup. I can't imagine the Rabbi Jesus and his talmids wandering around Galilee, Judea, and Jerusalem with a jewel encrusted and gold cladded goblet.

Agree but I could see some followers adding gold gilt and jewels to the "The Cup" after His death.

Exactly. As it happens, there's a simple stone cup that fits both the legend and the realities of historical Judea perfectly. According to Catholic history, Saint Peter carried a simple agate cup (a semi-translucent polished stone) which he used to perform communions. Agate was a popular material in ancient times for adornment and decoration. It wasn't as valuable as gold, but it was more valuable than simple terra cotta and would have been a nice piece for a Jewish household to celebrate Passover with. You may recall what the dinner was for, and why this fits. Peter himself claimed that the cup was the cup of the Last Supper, a cup which would later become known as the Holy Grail. The cup was used by early popes for centuries, before it was finally given to Lawrence (Lorenzo) to hide. At that point it "officially" disappears from history. Up to this point, it's all well recorded.

Shortly afterward, a guy named Proselius showed up on the doorstep of Lawrences parents home in Spain with a story and a treasure. Proselius held a simple agate cup which perfectly matched the description of the now-hidden Holy Chalice. When Lawrence realized that he was about to be arrested, he wrote a letter describing the cup, and gave it to Proselius, a Christian Roman soldier and a friend, and asked him to take it to Spain. After Pope Sixtus was executed, Saint Lawrence was ordered to turn over all the riches of the Church to the Emperor of Rome. He asked for three days to gather the treasures, which was granted. Instead of doing so, he gave the treasures away to the poor, and gave many of the more venerable items to friends for safekeeping. According to Ambrose, he was executed for defying the emperor. Shortly after that, Proselius turned up in Spain with a package for his parents. Inside was the simple agate cup, along with a letter explaining that this was the Holy Chalice and the cup that Christ drank from at the last supper. They took the cup and letter to a monastary, where it remained for the next thousand years. There's little documentation about it from this period, but apparently the monks who lived in the monastary during that period only existed to guard the chalice and the letter. After a thousand years, the cup changed hands a few times during some very well documented transfers between kings, before finally ending up in the Cathedral of Valencia, where it sits today.

People looking at the cup today see a beautiful golden chalice adorned with pearls, rubies, and other gems, topped with a small brown, almost dirty looking cup. What they often don't realize is that the gold is simply a base designed sometime in the middle ages to support a simple stone cup.

Personally, I think the hunt for the grail is nonsense. I believe it does exist, and it's sitting in a cathedral in Spain. The cup's design fits, it matches early descriptions of the Holy Chalice, and the story behind its transfer fits extremely well with known history.

Interestingly, unlike many so called "holy relics" that heal people in their waters, grant luck, or do a gazillion other supernatural things, there is no claims to supernatural powers surrounding the Chalice of Valencia. It's just a stone cup with a pretty base that Jesus happened to drink out of (if you believe the story, anyway).

"Agree but I could see some followers adding gold gilt and jewels to the "The Cup" after His death."

Or substituting another one entirely.