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Legal Seafood, as was mentioned, is awesome. Also try The Union Oyster House, Jimmy's, and The No Name. The latter two are down on the World Trade Center Pier. All are really good and a bit less expensive than Legals. If it were warmer I'd say go check out the Charles River area. Probably one of the most unique features of the city with sailing, kayaking, and rowing on it. Of course, I'm biased since I'm from there.
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I prefer desert wines to dessert wines.
Dry and red
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