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I don't think I've ever done a trip to NYC (business or pleasure) without hitting at least a few of these places...

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310 West Broadway, New York, NY, United States
New York, NY, US
(212) 965-3000
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Oldschool (relatively) and hip, with great views, food and an amazing location - close to shopping, dining and just general wandering, the SoHo Grand is one of my very favorite hotels in New York and otherwise.
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260 6th Avenue, New York, NY, United States
New York, NY, US
(212) 982-2343
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Small, cozy, friendly and lively, Silvano knows exactly what he's doing. This is some of the best Italian in New York and I make a point to visit Da Silvano whenever I find myself in the City. It's reasonably priced too. Rapine con salsiccia is fantastico, as is the tagliatelle bolognese. Ossobuco and one of the excellent Barolos offered here make dinner complete and perfetto.
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178 7th Avenue South, New York, NY, United States
New York, NY, US
(212) 255-4037
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Since 1935, the Village Vanguard has been the spot for the deepest, darkest corners of jazz and cool in America. Descend some rickety stairs into the basement hall where you'll hear guys blasting out classic and wildly erratic jazz, blues and the like. Enjoy your drinks, but don't talk - this crowd is here for the music.
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Prince Street
New York, NY, US

Still cool, still good after many years, the Mercer Kitchen is such a fantastic place to meet friends for drinks, dinner and generally hang out. A lively scene, ther Mercer serves up some excellent crab crostini and crunchy roasted haddock (2 of my favorites), and the drinks are good and strong. Never a dull evening at the Mercer Kitchen...
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August restaurant is a wood-fired paradise. There is nothing for me that approaches their egg dishes in cast iron skillets. Several varieties, and each one more amazing than the next. Combined with their artisan crusty bread, a mimosa and a delicious cup of their coffee, one can sit in their back "greenhouse" room and marvel at the leaves, rain or snow falling. Yes, August is best in the fall and winter of the year...
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