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Casual places near the Onyx Hotel

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Hi...My spouse and I are staying in Boston July 4 through 7th,at the Onyx Hotel.
I've read and appreciated the recent threads about great Italian places,as well as dining near the Park Plaza. Italian and seafood fare would probably be my first two choices.

On July 5th we plan to get together with an old friend whom I haven't seen in years.
I expect we'll meet at the hotel and walk from there. I'm hoping for some lively conversation
and an energetic walk before settling in for dinner.
Are reservations essential for a Saturday night?

Lastly,are there any staple or fun foods that we shouldn't miss trying,(or at least knowing about?) I'm thinking of wood fired bagels and poutine from Montreal,here.

Thanks for your suggestions...

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