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Recs for visitor from San Diego

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My brother is visiting from San Diego for a few days and I'd like to take him to restaurants that are quintessential Boston, or at least different or better than what they have in San Diego. I'm not too knowledgeable about the Boston scene myself being on a student budget, but willing to spend when he is visiting (Pigalle $$ - probably okay; O Ya$$$ - not ok). We are in Somerville, we have a car and are willing to drive. Recs for any meal appreciated. Thanks!

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  1. Some chow that he'll never get in SD, of any quality. Go to Chinatown for dim sum, Vinnie's in Sommerville for Italian, Regina's only in the North-end for pizza also Neptune. It's too late for clam shacks but, maybe The Causeway in Gloucester for some fresh seafood.

    1. My whole family lives in Florida so I try to do the same when they come to visit and they love anything that's quintessential New England.
      The Clam Box in Ipswich is a fave. Newburyport is not only home to some great restaurants but also a fun town to just walk around and kill time...I can recommend Aquatini, Michael's and Plum Island Grille there.
      Good places to go with good food/drinks and a trendy/20-30 something, attractive crowd are: The Beehive in the S. End, Fiore or Bricco in the North End, Match on Mass Ave, Sonsie on Newbury St.
      Also, Pho or Dim Sum in Chinatown I would 2nd that...I feel like Regina is very quintessential Boston and Boston Beer Works by Fenway is fun with some decent food.

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      Plum Island Grille
      2 Plum Island Blvd, Newbury, MA 01951

      Bricco
      241 Hanover St., Boston, MA 02113

      Clam Box
      789 Quincy Shore Dr, Quincy, MA 02170

      Boston Beer Works
      61 Brookline Ave Ste 2, Boston, MA 02215

      Aquatini
      27 State St, Newburyport, MA 01950