He was told that the show he was going be on would to air during a nautical-themed week sponsored by Carnival Cruise Line.

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"The instant I got my theme, I immediately came up with an ever-growing list of puzzles themed towards cruises, sailing, fish, boats -- anything on or in the water," Santoli told local Yorktown news site TAP Into.

Santoli said he looked at sites that track past puzzles, and took advantage of the show sometimes repeating themed puzzles.

Santoli was determined to make his appearance on the show pay off.

He first tried out for the show when he was 19 and tried several more times before making it on a taping.

When the first round started, Santoli studying was put to the test.

With only an ampersand and a D, Santoli guessed the first puzzle, "Port & Starboard," which had the category "places."

From there, the other players, Bonnie and Noelle, didn't have much of a chance.

"As soon as I solved the Round 1 puzzle for some cash and a $6,009 cruise, I knew they had a lot of catching up to do, so I told them, 'I'm sorry,'" Santoli said. "They were very nice, both before and after the show."

Santoli solved most of the puzzles and ended up making it to the bonus round, but he said host Pat Sajak spoke to him about his playing during a commercial break.

Santoli said Sajak told him, "That was great, Robert, but now we have to let someone else play, OK?"

CNN reported that at one point during the taping, Sajak asked Santoli to slow down on solving puzzles, saying, "Let it come up, then I guess you can tell us what's there."

After winning the second tossup puzzle and making it to the bonus round, Santoli spoke to his competitors.

"Before they walked off the set after the final round, I told them: 'No hard feelings.'"

By the end of the night, Santoli won two cruises, contributing to a total of $76,000 in cash and prizes.

Santoli plans on taking his mother on one of the southern Caribbean cruises and his father or sister on another.

As for his cash winnings? "I plan to pay off my student loans from Fordham (University) and buy or lease my own car," he said.

Watch Santoli's big win below.

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