A few examples for me: Meow Wolf (which I just visited, Santa Fe), Sleep No More (NYC), Cirque du Soleil Mystere (Las Vegas, far & away the best of the 5 or so I've seen), Midway Museum (aircraft carrier museum in San Diego).
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Probably worth excluding most entertainment-related answers (fly to watch band X) or similar things (food?) for better, er, interestingness-density
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If someone's really, genuinely willing to pay ~1k to fly to a city, get a hotel, arrange rides to-and-from airport, just to go to a restaurant, I'd like to know the name of that restaurant, and what's so awesome about it.
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Went to my tenth MIT Mystery Hunt (puzzle hunt) last year! It's in Boston, I live in CA now.
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Neat! Seems to inspire that devote in many people, must be awesome.
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I’ve flown to Chicago just to eat at Alinea a couple times now.
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Mona (tasmania)
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Wildlife. Whale watching in Baja, Safari in South Africa. On the todo list: polar bears, Galapagos.
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a good opera, unique art exhibition
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The calculation changes a fair bit if you factor in the carbon and are not good at working on trains...
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