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Trendy, tasty big-city dining with ladies out on the town

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Hello Chowhounds,
Two friends are coming into the city for the long upcoming weekend and I'm trying to convince one of them to move here. As such, I want to showcase delicious dining - one night in the North End, one night in the South End or Cambridge.
Where would you recommend?
I was thinking something along the lines of Dali in Somerville, or perhaps Gargoyles, or Masa - places along those lines, but maybe a bit more exciting. Help!

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  1. The first place that came to mind fitting these requirements would be Toro in the South End. It has a nice vibe and delicious twists on tapas (some are fairly traditional, other definitely not). A few highlights the last time I was there were the braised short ribs and smoked duck drummettes. The corn is delicious too - although a bit messy. The only problem is they do not take reservations so there might be a wait.

    1 Reply
    1. re: LauraB

      Eastern Standard Kitchen - great food, great bar, great vibe

    2. For your one night in the North End, I can't think of anyplace that consistently dazzles us with deliciousness more than Prezza.

      1. in the NE, Lucca or Przza
        in the SE, Toro, Hamersley's,

        1. I would go to the Liberty hotel and grab a drink and hang out in the lobby/lounge. I have heard that it is a real scene on the weekends. There is also a restaurant which is not bad (Clink) and the lounge downstairs (Alibi) which is awesome.

          Rocca or toro in the southend.

          Maybe Dante in Cambridge.

          1. I would second Hamersley's Bistro in the south end and Lucca in the north end.