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The Carnegie Club on W.56th is a classic. There's also Club Macanudo on the UES, 63rd street, I think. These are both serious cigar bars, which means old fat white men and lots and lots of smoke. If you want something younger and trendier, either Bar & Books is a better choice.
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IIRC Brandy Library allows smoking on the patio, but it's quite small.
There's also Hudson Bar & Books.
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re: kathryn
And its sister restaurant, Lexington Bar & Books (not as frou frou as the website would have you think).
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