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Most expensive drink was relative - 9,000 yen for a beer at the Hard Rock Cafe at Uneo station in Tokyo. That's almost $9.00. It WAS St. Patrick's day and it WAS a Guinness.
My wife hit me up for an 'aged' snifter of Grand Marnier @ the Redwood Room (@ the Clift Hotel) our first trip to San Francisco, several years ago. I believe it was $26.