This ought to be fun!
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Houston Ag,
I feel the 21 Club is overrated with regard to the food, but the place is worth a look due to it's history as a speakeasy.
I highly recommend River Cafe in Brooklyn. Very good food and great views from under the Brookyn Bridge. Make sure to request a table closest to the windows so you can get as much of the view as possible.
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an average restaurant in Manhattan will be between $150 and $200 for two people with a bottle of wine and gratuity.